Methanol → Methyl 2-(4-bromophenyl)acetate

HRID 1401890Notes

Reaction equation

HRID 1401890 reaction equation
S(=O)(=O)(O)O.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1.[CH3:17]O>>[CH3:17][O:15][C:14](=[O:16])[CH2:13][C:10]1[CH:9]=[CH:8][C:7]([Br:6])=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 887Methanol2×HCID 1118Sulfuric AcidHCID 74654Benzeneacetic acid, 4-bromo-

Product 1

HCID 316783Methyl 2-(4-bromophenyl)acetateYield 98%

Procedure

Sulfuric acid (56.5 mL) was very slowly added to a solution of 206.6 g of 4-bromophenyl acetic acid in methanol (800 mL). After completion of the addition, the mixture was heated to reflux for 2 h. The reflux condenser was replaced by a distillation head and 400 mL of methanol was atmospherically distilled. The temperature was the reduced to 50° C. and the reaction stirred for additional 16 h, when the mixture was then cooled to room temperature and partitioned between dichloromethane (1 L) and water (600 mL). The organic phase was washed with saturated sodium bicarbonate and dried over magnesium sulfate. Concentration under reduced pressure provided 220.1 g (98% yield) colorless oil. HNMR: CDCl3, 3.59 (s, 2H), 3.70 (s, 3H), 7.16 (d, 2H), 7.45 (d, 2H)

Workup

  1. additionAfter completion of the addition
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 2 h
  4. distillationwas atmospherically distilled
  5. customreduced to 50° C.
  6. custompartitioned between dichloromethane (1 L) and water (600 mL)
  7. washThe organic phase was washed with saturated sodium bicarbonate
  8. dry with materialdried over magnesium sulfate
  9. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-14e8f6b380e3426a812d62b72fe98587
Source dataset
uspto-grants-2014_12
Patent number
US08907103B2

Reaction notes

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