Benzyl Bromide → (4-Chloro-2-phenylmethoxyphenyl)methanol

HRID 878611Notes

Reaction equation

HRID 878611 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:17][OH:18])=[C:14]([OH:16])[CH:15]=1.[OH-].[Na+]>C(O)C>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:17][OH:18])=[C:14]([O:16][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:15]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 3271485-Chloro-2-(hydroxymethyl)phenol

Product 1

HCID 58083510(4-Chloro-2-phenylmethoxyphenyl)methanolYield 28%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(Bromomethyl)benzene (323 mg, 1.89 mmol) was added to a mixture of 5-chloro-2-(hydroxymethyl)phenol (300 mg, 1.89 mmol, PREPARATION 7) and NaOH (1.1 mL, 2M in water) in ethanol (5 mL) at r.t. slowly. The reaction mixture was stirred overnight. Poured into ice water, and extracted with ethyl acetate twice, and washed the organic phase with water twice, brine and dried with anhydrous Na2SO4. The solvents were removed and the residue purified by silica gel chromatograph to give 120 mg of the title compound (28%).

Workup

  1. extractionextracted with ethyl acetate twice
  2. washwashed the organic phase with water twice
  3. dry with materialbrine and dried with anhydrous Na2SO4
  4. customThe solvents were removed
  5. customthe residue purified by silica gel chromatograph

Sources & evidence

ORD record
ord-b2ef4df66e9e46189ad15008c70b4f67
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

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