Methanol → Methyl 2-(4-bromophenyl)acetate

HRID 1372438Notes

Reaction equation

HRID 1372438 reaction equation
S(Cl)(Cl)=O.[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=[O:14])=[CH:8][CH:7]=1.[CH3:16]O>>[Br:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 887Methanol2×HCID 24386Thionyl ChlorideHCID 74654Benzeneacetic acid, 4-bromo-

Product 1

HCID 316783Methyl 2-(4-bromophenyl)acetateYield 100%

Procedure

Thionyl chloride (18 mL, 0.25 mol) was added dropwise to a solution of 4-bromo-phenylacetic acid (50 g; 0.23 mol) in methanol (250 mL). The resulting mixture was stirred at room temperature for 1 hour before the methanol was removed in vacuo. Ethyl acetate (300 mL) was added and the resulting solution was washed with water (3×150 mL) and 1M aqueous NaHCO3 (1×150 mL), dried (MgSO4) and evaporated to give the ester (52.8 g; 100%) as an orange oil which was used without further purification.

Workup

  1. customwas removed in vacuo
  2. additionEthyl acetate (300 mL) was added
  3. washthe resulting solution was washed with water (3×150 mL) and 1M aqueous NaHCO3 (1×150 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-d21ae83636a241a88899cc4a4340bdd9
Source dataset
uspto-grants-2007_01
Patent number
US07157585B2

Reaction notes

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