Methanol → Methyl 2-(3-bromophenyl)acetate

HRID 2412254Notes

Reaction equation

HRID 2412254 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.[CH3:17]O>>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:17])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 74653(3-Bromophenyl)acetic acid

Product 1

HCID 11746402Methyl 2-(3-bromophenyl)acetateYield 91%

Procedure

A stirred solution of (3-bromophenyl)acetic acid (10.0 g, 0.0465 mol) and concentrated sulfuric acid (4.5 mL) in MeOH (230 mL) was heated at 40° C. for 16 h. The reaction mixture was concentrated under reduced pressure and the residue was mixed with water (50 mL) and DCM (100 mL). The layers were separated and the organic layer was concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-10% EtOAc/hexanes) to give the title compound (19.8 g, 91% yield) as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was mixed with water (50 mL) and DCM (100 mL)
  3. customThe layers were separated
  4. concentrationthe organic layer was concentrated under reduced pressure
  5. customThe residue was purified by silica gel flash chromatography (0-10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-0556ab2d5211424ea817511dcc9159db
Source dataset
uspto-grants-2014_08
Patent number
US08816088B2

Reaction notes

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