Benzyl Bromide → HCID 58083510, compound

HRID 514454

Reaction equation

HRID 514454 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 58083510HCID 58083510, compoundYield 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-bd2a2b399d87489caf3a31043675f9b3
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Linked notes

Loading…