Dichloromethane → HCID 59627740, compound

HRID 1930127Notes

Reaction equation

HRID 1930127 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=[O:15])=[CH:9][C:8]=1[C:17]([F:20])([F:19])[F:18].Cl[CH2:22]Cl>>[OH:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([O:16][CH3:22])=[O:15])=[CH:9][C:8]=1[C:17]([F:20])([F:19])[F:18]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 46737531[4-Methoxy-3-(trifluoromethyl)phenyl]acetic acid

Product 1

HCID 59627740HCID 59627740, compoundYield 33.2%

Procedure

Boron tribromide (8.02 mL, 84.87 mmol) was added dropwise to 2-(4-methoxy-3-(trifluoromethyl)phenyl)acetic acid (3.31 g, 14.13 mmol) in dichloromethane (250 mL) while maintaining the temperature below 10° C. After complete addition the reaction mixture was removed from the ice bath and allowed to stir at ambient temperature under nitrogen for 90 minutes. The reaction mixture was added dropwise to ice cold methanol (150 mL) and the mixture was stirred at ambient temperature for a further 40 minutes. The reaction mixture was evaporated to afford to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford methyl 2-(4-hydroxy-3-(trifluoromethyl)phenyl)acetate (1.100 g, 33.2%) as a pale yellow oil.

Workup

  1. temperaturewhile maintaining the temperature below 10° C
  2. additionAfter complete addition the reaction mixture
  3. customwas removed from the ice bath
  4. additionThe reaction mixture was added dropwise to ice cold methanol (150 mL)
  5. stirringthe mixture was stirred at ambient temperature for a further 40 minutes
  6. customThe reaction mixture was evaporated
  7. customto afford
  8. customto afford crude product
  9. customThe crude product was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in isohexane
  10. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-60e1409951054af4b8a53644b65967fe
Source dataset
uspto-grants-2012_05
Patent number
US08188092B2

Reaction notes

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