Methanol → Methyl 4-bromo-2-phenylbutanoate

HRID 1780214Notes

Reaction equation

HRID 1780214 reaction equation
[Br:1][CH2:2][CH2:3][CH:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:5]([OH:7])=[O:6].O=S(Cl)Cl.[CH3:18]O>>[Br:1][CH2:2][CH2:3][CH:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:5]([O:7][CH3:18])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 167406054-Bromo-2-phenylbutanoic acid

Product 1

HCID 19050128Methyl 4-bromo-2-phenylbutanoate

Procedure

The product of Example 4 (22 g) in methanol (100 ml) was treated dropwise with SOCl2 (7.3 ml, 0.1M) at about 5° C. The reaction mixture was allowed to warm to room temperature. The solvent was evaporated off and the residue partitioned between water and IPE. The organic phase was dried and evaporated to give the title compound as an oil (23 g). Bp. 85°/0.1 mm.

Workup

  1. customThe solvent was evaporated off
  2. customthe residue partitioned between water and IPE
  3. customThe organic phase was dried
  4. customevaporated

Sources & evidence

ORD record
ord-81fd257f56594f56b78e27be41d8ad80
Source dataset
uspto-grants-1997_05
Patent number
US05629432

Reaction notes

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