Water → HCID 15065645, compound

HRID 466484Notes

Reaction equation

HRID 466484 reaction equation
B(Br)(Br)Br.[C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=2)=[CH:9][C:8]=1[F:21])#[N:6].O>ClCCl>[C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[CH:9][C:8]=1[F:21])#[N:6]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 27633572-fluoro-4-(4-methoxyphenyl)benzonitrile

Product 1

HCID 15065645HCID 15065645, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of boron tribromide (12.0 ml, 31.8 g, 0.13 mol) in dry dichloromethane (100 ml) was added dropwise to a stirred, cooled (-78° C.) solution of compound 4 (14.0 g, 0.06 mol) in dry dichloromethane (250 ml) under dry nitrogen. The stirred mixture was allowed to warm. to room temperature over 20 h (i.e., until glc analysis revealed absence of starting material). Water was added and a yellow precipitate was produced. The product was extracted into ether (twice), and the combined ethereal extracts were washed with water and dried (MgSO4). The solvent was removed in vacuo to afford a pale-yellow powder.

Workup

  1. temperatureto warm
  2. customa yellow precipitate was produced
  3. extractionThe product was extracted into ether (twice), and the combined ethereal extracts
  4. washwere washed with water
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo
  7. customto afford a pale-yellow powder

Sources & evidence

ORD record
ord-44de8140876e4c7699fabb2788d9ec39
Source dataset
uspto-grants-1992_10
Patent number
US05156763

Reaction notes

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