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

HRID 1746101Notes

Reaction equation

HRID 1746101 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:9][OH:10])=[C:6]([OH:8])[CH:7]=1.[OH-].[Na+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C.O.ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:9][OH:10])=[C:6]([O:8][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:7]=1

Participants

7

Reactant 3

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

Product 1

HCID 58083510(4-Chloro-2-phenylmethoxyphenyl)methanol

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-chloro-2-(hydroxymethyl)phenol (for a preparation see intermediate 5; 1.51 g, 9.54 mmol) in ethanol (20 ml), was added sodium hydroxide (5.25 ml, 10.5 mmol). To the mixture was added a solution of benzyl bromide (Aldrich; 1.14 ml, 9.54 mmol) in ethanol (30 ml) dropwise. The reaction was stirred under nitrogen overnight at ambient temperature. The solvent was removed in vacuo to leave an aqueous suspension. The suspension was diluted with water (50 ml) and dichloromethane (40 ml). The phases were separated and the aqueous phase extracted with dichloromethane (30 ml). The combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate (20 ml) and the solvent removed in vacuo to leave a white solid (1.52 g). The residue was loaded in dichloromethane and purified on silica (100 g) using 0-50% ethyl acetate-cyclohexane. The appropriate fractions were combined and evaporated in vacuo to give the title compound (1.32 g) as a white solid; LCMS (System 2): (M-H)−=247, tRET=1.17 min.

Workup

  1. customThe solvent was removed in vacuo
  2. customto leave an aqueous suspension
  3. customThe phases were separated
  4. extractionthe aqueous phase extracted with dichloromethane (30 ml)
  5. washThe combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate (20 ml)
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-dbf4500bc20d4d85b00d963423f046db
Source dataset
uspto-grants-2015_10
Patent number
US09149462B2

Reaction notes

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