Boron tribromide → HCID 69117604, compound

HRID 902389Notes

Reaction equation

HRID 902389 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:20]C)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:7]=1.B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:5]([OH:20])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 69117197HCID 69117197, compound

Product 1

HCID 69117604HCID 69117604, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-fluoro-2-methoxy-2′-phenylbiphenyl (7.3 g, 26.2 mmol) in methylene chloride (100 mL) cooled to −78° C. was added through syringe boron tribromide (1.0 M in dichloromethane, 40.0 mL, 40.0 mmol). The reaction mixture was stirred and allowed to warm up to room temperature overnight. The resulting mixture was diluted with dichloromethane, washed with water and saturated sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by ISCO using a solvent gradient of 0 to 40% ethyl acetate in hexanes provided 6.8 g (98%) of 5-fluoro-2′-phenylbiphenyl-2-ol as a light brown oil.

Workup

  1. washwashed with water and saturated sodium chloride
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customPurification by ISCO

Sources & evidence

ORD record
ord-1268e28cfcf84092a4a2364799dfbcc9
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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