Methanol → Methyl 2-(4-bromophenyl)acetate

HRID 2189130Notes

Reaction equation

HRID 2189130 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.S(Cl)(Cl)=O.[CH3:16]O>>[CH3:16][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

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 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) was added dropwise thionyl chloride (34.2 mL) while the temperature of the reaction mixture was kept at 0-5° C. Upon complete addition cooling was stopped and the mixture was allowed to warm to rt. Stirring was continued for 75 min before the solvent was removed in vacuo. The yellow oil was dissolved in benzene and again concentrated. The residue was dissolved in EA, washed with water, brine, 2 N aq. Na2CO3, and again brine. The org. extract was dried over MgSO4, filtered, concentrated and dried under HV at 85° C. for 30 min to give the expected product as a yellow oil (52.4 g).

Workup

  1. customwas kept at 0-5° C
  2. additionUpon complete addition
  3. temperaturecooling
  4. customwas removed in vacuo
  5. dissolutionThe yellow oil was dissolved in benzene
  6. concentrationagain concentrated
  7. dissolutionThe residue was dissolved in EA
  8. washwashed with water, brine, 2 N aq. Na2CO3, and again brine
  9. extractionextract
  10. dry with materialwas dried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customdried under HV at 85° C. for 30 min

Sources & evidence

ORD record
ord-7ca8518b25ea472bb334b47c2d20df9d
Source dataset
uspto-grants-2012_12
Patent number
US08324232B2

Reaction notes

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