Dimethylformamide → Methyl 3-bromo-4-methylbenzoate

HRID 230013

Reaction equation

HRID 230013 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].[C:12](Cl)(=O)C(Cl)=O.CN(C)C=O>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([O:7][CH3:12])=[O:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 821303-Bromo-4-methylbenzoic acid

Product 1

HCID 7015747Methyl 3-bromo-4-methylbenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.0 g (9.3 mmol) of 3-bromo-4-methylbenzoic acid in 25 mL of dichloromethane was added 5.6 mL (11.2 mmol) of oxalyl chloride and 100 μL of N,N-dimethylformamide. The resultant mixture was stirred at ambient temperature for 2 hours, concentrated in vacuo, and the residue suspended in methanol. The solution was concentrated in vacuo and the residue purified by flash column chromatography (biotage) using 5% ethyl acetate/hexanes as eluent to provide the title compound. 1H NMR (500 MHz, CDCl3) δ 8.23 (s, 1H), 7.90 (d, 1H, J=8 Hz), 7.33 (d, 1H, J=8 Hz), 3.94 (s, 3H), 2.48 (s, 3H). HPLC/MS (ESI) m/z (M+H)=231.0 (3.63 min).

Workup

  1. concentrationconcentrated in vacuo
  2. concentrationThe solution was concentrated in vacuo
  3. customthe residue purified by flash column chromatography (biotage)

Sources & evidence

ORD record
ord-423413aeb8754121ad761b8f9d2cf227
Source dataset
uspto-grants-2009_07
Patent number
US07563815B2

Linked notes

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