Electric Literature of 53087-13-1, The chemical industry reduces the impact on the environment during synthesis 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, I believe this compound will play a more active role in future production and life.
Step 1 : Preparation of tert- utyl 4-(3-Benzyloxyphenyl)-4-hydroxypiperidine-l- carboxylate. A suspension of magnesium metal (0.144g, 6.0 mmol) in THF (10 mL) was rapidly stirred for 30 minutes under nitrogen then a solution of 3-benzyloxybromobenzene (1.58g, 6.00 mmol) in THF (10 mL) added slowly via dropping funnel. Once approximately 1 mL of the bromide solution had been added a crystal of iodine was added to the reaction and the mixture gently heated until Grignard formation began. The remaining bromide solution was then added at a rate to maintain a reaction temperature range of 50-60 C. Once addition was complete the reaction was heated to gentle reflux for 1 hour then cooled in an ice bath. A solution of tert- utyl 4-oxopiperidine-l-carboxylate (l .OOg, 5.02 mmol) in THF (10 mL) was the added to the reaction over a period of 30 minutes then the mixture was allowed to warm to room temperature with stirring over a 2 hour period. After this time the reaction was quenched by the addition of 25% ammonium chloride solution (50 mL) and the layers separated. The aqueous was extracted with ethyl acetate (2 x 10 mL) and the combined organics were washed with water (20 mL) and brine (20 mL) then dried over magnesium sulfate. Subsequent filtration, concentration and purification of the residue by column chromatography (Si02, 0-25% ethyl acetate /heptanes) afforded a 61 % yield of tert- butyl 4-(3-benzyloxyphenyl)-4-hydroxypiperidine-l-carboxylate as a viscous clear oil that became a white solid on standing.1H NMR (CDC13): delta = 7.41-7.33 (m, 5H), 7.29 (d, J = 7.3 Hz, 1H), 7.15 (t, J = 1.9 Hz, 1H), 7.06 (d, J = 7.8 Hz, 1H), 6.91 (dd, J = 8.0, 2.1Hz, 1H), 5.09 (s, 2H), 4.03 (m, 2H), 3.25 (bt, J = 12Hz, 2H), 2.00 (bt, J = 11.1Hz, 2H), 1.73 (bd, J= 12.6Hz, 2H) and 1.50 ppm (s, 9H).
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-(Benzyloxy)-3-bromobenzene, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; KINENTIA BIOSCIENCES LLC; FAIRFAX, David J.; WO2011/137331; (2011); A2;,
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