Methanol → Methyl 2-(3-bromophenyl)acetate

HRID 563616Notes

Reaction equation

HRID 563616 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(Cl)(Cl)=O.[CH3:16]O>>[CH3:16][O:10][C:9](=[O:11])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 74653(3-Bromophenyl)acetic acid

Product 1

HCID 11746402Methyl 2-(3-bromophenyl)acetate

Conditions

Temperature
65 °C

Procedure

To 3-bromophenylacetic acid (5.03 g, 23.4 mmol) in MeOH (50 mL) was added thionyl chloride (3.4 mL, 46.8 mmol), and the reaction was stirred at 65° C. for 5 hours. The mixture was concentrated, and the residue was partitioned between CH2Cl2 and saturated aqueous NaHCO3. The mixture was basified with 1N aqueous NaOH, and the aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with H2O, dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was partitioned between CH2Cl2 and saturated aqueous NaHCO3
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. washThe combined organic layers were washed with H2O
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e0c7a9dfb77d4582a33d010544b17067
Source dataset
uspto-grants-2011_11
Patent number
US08067445B2

Reaction notes

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