Methanol → Methyl 3-bromo-2-methoxybenzoate

HRID 1889707Notes

Reaction equation

HRID 1889707 reaction equation
[Br:1][C:2]1[C:3]([O:11][CH3:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[C:13](Cl)(=O)C(Cl)=O.CO>C(Cl)Cl.N1C=CC=CC=1>[Br:1][C:2]1[C:3]([O:11][CH3:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:13])=[O:6]

Participants

6

Reactant 3

HCID 887MethanolHCID 65578Oxalyl chlorideHCID 2535983-Bromo-2-methoxybenzoic acid

Product 1

HCID 46311082Methyl 3-bromo-2-methoxybenzoateYield 90%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-Bromo-2-methoxybenzoic acid (2 g, 8.65 mmol, 1.0 eq) was dissolved in dry DCM and stirred for 10 minutes, cooled to 0° C. and slowly treated with oxalyl chloride (3.3 g, 25.9 mmol, 3 eq). Methanol in pyridine was added dropwise and the reaction mixture was stirred at ambient temperature. The solvents were evaporated under reduced pressure and the reaction mass was diluted with water. The aqueous mixture was extracted with ethyl acetate. The organic layer was dried with anhydrous Na2SO4 and concentrated under vacuum to afford the desired product (1.9 g, 90%). 1H NMR (400 MHz, CDCl3) δ 3.93 (s, 6H), 7.02-6.06 (t, 1H), 7.72-7.76 (m, 2H). MS (ESI): 247.0 (M+H)+.

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature
  2. customThe solvents were evaporated under reduced pressure
  3. additionthe reaction mass was diluted with water
  4. extractionThe aqueous mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried with anhydrous Na2SO4
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a6554cb1f3c542b18c5d0618c7683390
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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