Acetyl chloride → Methyl 4-bromo-2-methylbenzoate

HRID 2356787Notes

Reaction equation

HRID 2356787 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1.[C:12](Cl)(=O)C>CO>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:12])=[O:7])=[C:4]([CH3:11])[CH:3]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 995704-Bromo-2-methylbenzoic acid

Product 1

HCID 22031226Methyl 4-bromo-2-methylbenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Bromo-2-methylbenzoic acid (2.00 g, 9.30 mmol) was added to a solution of acetyl chloride (1.70 mL, 23.9 mmol) in methanol (30 mL). The mixture was allowed to stir at rt for 3 days and was then concentrated in vacuo. This gave 1.96 g (92%) of the title compound as a light brown oil. 1H NMR (400 MHz, CD2Cl2) 2.61 (s, 3H), 3.90 (s, 3H), 7.38-7.42 (m, 2H), 7.78 (d, 1H).

Workup

  1. concentrationwas then concentrated in vacuo

Sources & evidence

ORD record
ord-59d7ccd774cd4788ba5cae219831f54f
Source dataset
uspto-grants-2010_07
Patent number
US07759376B2

Reaction notes

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