Water → 2-(Bromomethyl)-4'-chlorobiphenyl

HRID 1750741Notes

Reaction equation

HRID 1750741 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14]O)=[CH:4][CH:3]=1.[Li+].[Br-].P(Br)(Br)[Br:19].O>CN(C=O)C>[Br:19][CH2:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24614Phosphorus tribromideHCID 82050Lithium BromideHCID 13927802-(4-Chlorophenyl)benzyl alcohol

Product 1

HCID 582376872-(Bromomethyl)-4'-chlorobiphenyl

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of Example 37A (7.9 g) and LiBr (3.45 g) in DMF (100 mL) at 0° C. was added PBr3 (3.77 mL) and the reaction was stirred for 1 hour. The reaction was poured into water (400 mL), and the mixture was extracted with ether (3×200 mL). The combined ether layers were washed with 3× water, and brine, dried over Na2SO4, and condensed to give the title compound.

Workup

  1. extractionthe mixture was extracted with ether (3×200 mL)
  2. washThe combined ether layers were washed with 3× water, and brine
  3. dry with materialdried over Na2SO4, and condensed

Sources & evidence

ORD record
ord-580c61c0c1cb4133a3ad71422e7974b7
Source dataset
uspto-grants-2015_10
Patent number
US09156856B2

Reaction notes

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