Bromine → HCID 22752732, compound

HRID 1480637Notes

Reaction equation

HRID 1480637 reaction equation
[Br:1]Br.[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1>ClCCl.C(#N)C>[Br:1][C:12]1[CH:11]=[C:10]([C:7]2[CH:6]=[CH:5][C:4]([F:3])=[CH:9][CH:8]=2)[CH:15]=[CH:14][C:13]=1[OH:16]

Participants

5

Reactant 2

HCID 24408BromineHCID 3454204-Fluoro-4'-hydroxybiphenyl

Product 1

HCID 22752732HCID 22752732, compoundYield 117.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of bromine (4.57 g, 28.59 mmol) in dichloromethane (20 mL) was added dropwise to a solution of 4-fluoro-4′-hydroxybiphenyl [purchased from TCI] (5.38 g, 28.59 mmol) in dichloromethane (100 mL) and acetonitrile (20 mL) and the reaction mixture stirred at room temperature under nitrogen for 18 hours. The reaction mixture was washed with saturated aqueous sodium hydrogen carbonate solution (200 mL) containing 10% aqueous sodium thiosulfate solution (20 mL), water (200 mL) and saturated brine (200 mL), dried (MgSO4), filtered and concentrated in vacuo to give crude 3-bromo-4′-fluoro-[1,1′-biphenyl]-4-ol (9.0 g) as a tan solid.

Workup

  1. washThe reaction mixture was washed with saturated aqueous sodium hydrogen carbonate solution (200 mL)
  2. additioncontaining 10% aqueous sodium thiosulfate solution (20 mL), water (200 mL) and saturated brine (200 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6e7e4aedbcd04aad9d8197f76d13d6ea
Source dataset
uspto-grants-2016_08
Patent number
US09409893B2

Reaction notes

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