Boron tribromide → 2',6'-Dichloro-5-fluorobiphenyl-2-ol

HRID 902320Notes

Reaction equation

HRID 902320 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[O:16]C.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:10]([OH:16])=[CH:11][CH:12]=[C:13]([F:15])[CH:14]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 586469552',6'-Dichloro-5-fluoro-2-methoxybiphenyl

Product 1

HCID 691179112',6'-Dichloro-5-fluorobiphenyl-2-olYield 98.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2′,6′-dichloro-5-fluoro-2-methoxybiphenyl (12.44 g, 46 mmol) in methylene chloride (200 mL) was added boron tribromide (10.8 mL, 92 mol) at −78° C. The resulting mixture was stirred at −78° C. to room temperature overnight. The reaction mixture was poured into the ice-NH4OH and extracted with methylene chloride. The organic layer was washed with water and dried over anhydrous sodium sulfate and filtered. The solvent was removed under vacuum. Chromatography with 10–40% ethyl acetate in hexanes afforded 11.63 g (98%) of 2′,6′-dichloro-5-fluorobiphenyl-2-ol as a colorless oil. MS (ES) m/z 255.1([M−H]−).

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-eabd49b20d7c46bd807aeaaaa9605ec7
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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