Continuously updated synthesis method about 1-Bromo-2,3,4-trimethoxybenzene

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-Bromo-2,3,4-trimethoxybenzene, other downstream synthetic routes, hurry up and to see.

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General procedure: Aryl bromide (1.00 mmol; in case it is solid), Pd(PhCN)2Cl2 (11.5 mg, 0.030 mmol) and CuI (3.8 mg, 0.020 mmol) are added to a dry, 10-mL round bottom flask, which is then sparged with argon and charged with dioxane (1.0 mL; Aldrich Sure/Seal anhydrous/99.8%). P(t-Bu)3 (70 muL of a 1 M solution in dioxane; 0.07 mmol; made from 1gm P(t-Bu)3 and 4.95 mL anhydrous dioxane; preserved under argon), HN(i-Pr)2 (170 muL, 1.20 mol; freshly distilled over CaH2), aryl bromide (1.00 mmol, in case it is liquid), and the trimethylsilylacetylene (1.20 mmol) are added via syringe to the stirred reaction mixture. After the aryl bromide has been consumed, the reaction mixture is diluted with EtOAc (5 mL), filtered through a small pad of Celite (with EtOAc rinsings), concentrated in reduced pressure and silica gel (1 g) was added. Further evaporation lead to a silica gel plug which was loaded on top of a silica gel column (2 cm × 20 cm) and eluted with 5% ethyl acetate in hexanes. Fractions corresponding to the product spot were evaporated under reduced pressure to obtain analytically pure product.

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-Bromo-2,3,4-trimethoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Gangjee, Aleem; Namjoshi, Ojas A.; Keller, Staci N.; Smith, Charles D.; Bioorganic and Medicinal Chemistry; vol. 19; 14; (2011); p. 4355 – 4365;,
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