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Water → Ethyl 3-(2'-fluoro-5'-hydroxyphenyl)propionate

HRID 709701
Notes
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Reaction equation

HRID 709701 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8]C)=[CH:4][C:3]=1[CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].B(Br)(Br)Br.O>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 68536561Ethyl 3-(2'-fluoro-5'-methoxyphenyl)propionate

Product 1

HCID 68536248Ethyl 3-(2'-fluoro-5'-hydroxyphenyl)propionateYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-15 °C

Procedure

To a solution of ethyl 3-(2-fluoro-5-methoxyphenyl)propanoate (100 mg) in dichloromethane (3.0 mL) was added dropwise a 1.0 M solution of boron tribromide in dichloromethane (0.15 mL) at −15° C., and the mixture was stirred at −15° C. for 5 hr. Water (20 ml) was added dropwise to the reaction mixture, and the mixture was extracted with dichloromethane. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (60 mg) as a colorless oil. This compound was used for the next step without further purification.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-26afe13a7675468eb13611797f096131
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09181186B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes