Methanol → Methyl 2-(3-bromophenyl)acetate

HRID 456203Notes

Reaction equation

HRID 456203 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 (5.027 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. Once no starting material was seen by analytical LCMS, the mixture was concentrated and the residue was partitioned between CH2Cl2 and saturated aqueous NaHCO3. 1N Aqueous NaOH was added to adjust the pH to basic, and the aqueous layer was separated and 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. addition1N Aqueous NaOH was added
  4. customwas separated
  5. extractionextracted with CH2Cl2
  6. washThe combined organic layers were washed with H2O
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-196a0f4fbb224090ac672ea3067c44fa
Source dataset
uspto-grants-2013_07
Patent number
US08497381B2

Reaction notes

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