Water → 4-Cyano-3,5-difluoro-4'-hydroxybiphenyl

HRID 466487Notes

Reaction equation

HRID 466487 reaction equation
B(Br)(Br)Br.[C:5]([C:7]1[C:12]([F:13])=[CH:11][C:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=2)=[CH:9][C:8]=1[F:22])#[N:6].O>ClCCl>[C:5]([C:7]1[C:8]([F:22])=[CH:9][C:10]([C:14]2[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=2)=[CH:11][C:12]=1[F:13])#[N:6]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 150656534-Cyano-3,5-difluoro-4'-methoxybiphenyl

Product 1

HCID 150656544-Cyano-3,5-difluoro-4'-hydroxybiphenyl

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of boron tribromide (25.0 ml, 61.5 g, 0.25 mol) in dry dichloromethane (140 ml) was added dropwise to a stirred, cooled (-78° C.) solution of compound 8 (12.22 g, 0.05 mol) in dry dichloromethane (250 ml) under dry nitrogen. The stirred mixture was allowed to warm to room temperature over 9 h (i.e., until glc analysis revealed absence of starting material). The mixture was cooled to -10° C., water was added slowly (exothermic) and cooled to 2° C. The product was filtered off, washed with water and dried (CaCl2) in vacuo to give a pale-yellow powder.

Workup

  1. temperatureThe mixture was cooled to -10° C.
  2. temperaturecooled to 2° C
  3. filtrationThe product was filtered off
  4. washwashed with water
  5. dry with materialdried (CaCl2) in vacuo
  6. customto give a pale-yellow powder

Sources & evidence

ORD record
ord-d003d24366cb486580e2d9eb6c1f3b85
Source dataset
uspto-grants-1992_10
Patent number
US05156763

Reaction notes

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