Methanol → Methyl 2-(3-bromophenyl)acetate

HRID 1468496Notes

Reaction equation

HRID 1468496 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-1538a304222b4a8ab3d425c53831fb61
Source dataset
uspto-grants-2015_04
Patent number
US09000173B2

Reaction notes

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