Methanol → Methyl 3-bromo-5-methoxybenzoate

HRID 1845252Notes

Reaction equation

HRID 1845252 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[C:5]([OH:7])=[O:6].[CH3:13]N(C=O)C.C(Cl)(=O)C.CO>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[C:5]([O:7][CH3:13])=[O:6]

Participants

6

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 6367Acetyl chlorideHCID 40600483-Bromo-5-methoxybenzoic acid

Product 1

HCID 15618226Methyl 3-bromo-5-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of crude 3-bromo-5-methoxybenzoic acid (40% purity, 0.8 g, 1.4 mmol) in CH2Cl2 (50 mL) at 0° C. were added DMF (0.1 mL) and acetyl chloride (0.2 mL, 3 mmol). The mixture was slowly warmed to rt and stirred overnight. Then the mixture was cooled to 0° C. and methanol (2 mL) was slowly added. The mixture was stirred at rt for 3 h and then washed with aq. Na2CO3 solution, brine, dried (Na2SO4), and concentrated. The residue was purified via flash chromatography to afford the desired product as a white solid. 1H NMR (CDCl3, 400 MHz): 7.76 (t, J=1.6 Hz, 1H), 7.49 (t, J=1.3 Hz, 1H), 7.24 (t, J=2.2 Hz, 1H), 3.92 (s, 3H), 3.84 (s, 3H).

Workup

  1. temperatureThen the mixture was cooled to 0° C.
  2. stirringThe mixture was stirred at rt for 3 h
  3. washwashed with aq. Na2CO3 solution, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified via flash chromatography

Sources & evidence

ORD record
ord-351c631cae844a28ae88d4f4af905126
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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