Methanol → Methyl 2-(4-bromophenyl)acetate

HRID 251883Notes

Reaction equation

HRID 251883 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH3:12]O>>[CH3:12][O:10][C:9](=[O:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 74654Benzeneacetic acid, 4-bromo-

Product 1

HCID 316783Methyl 2-(4-bromophenyl)acetate

Procedure

To a solution of 4-bromophenylacetic acid (50 g) in methanol (250 mL) thionyl chloride (34.2 mL) is added dropwise while the temperature of the reaction mixture is kept at 0-5° C. Upon complete addition, the cooling is removed and the mixture is allowed to warm to rt. Stirring is continued for 75 min before the solvent is removed in vacuo. The yellow oil is dissolved in benzene and evaporated. The residue is dissolved in EA, washed with water, brine, 2 N aq. Na2CO3, and brine. The organic phase is dried over MgSO4 and evaporated and dried under high vacuum at 85° C. for 30 min to give 4-bromophenylacetic acid methyl ester (52.4 g) as a yellow oil. 1H-NMR(D6-DMSO): 3.60 (s, 3H), 3.67 (s, 2H), 7.22 (d, 8.5, 2H), 7.50 (d, 8.5, 2H).

Workup

  1. customis kept at 0-5° C
  2. additionUpon complete addition
  3. customthe cooling is removed
  4. customis removed in vacuo
  5. dissolutionThe yellow oil is dissolved in benzene
  6. customevaporated
  7. dissolutionThe residue is dissolved in EA
  8. washwashed with water, brine, 2 N aq. Na2CO3, and brine
  9. dry with materialThe organic phase is dried over MgSO4
  10. customevaporated
  11. customdried under high vacuum at 85° C. for 30 min

Sources & evidence

ORD record
ord-d974beee140a4455bcd90fd7cad827b9
Source dataset
uspto-grants-2011_01
Patent number
US07868012B2

Reaction notes

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