Benzyl Alcohol → 1-Bromo-4-phenylmethoxybenzene

HRID 2249274Notes

Reaction equation

HRID 2249274 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Br:11][C:12]1[CH:19]=[CH:18][C:15](CBr)=[CH:14][CH:13]=1.[Cl-].[NH4+]>CN(C)C=O>[CH2:3]([O:10][C:15]1[CH:18]=[CH:19][C:12]([Br:11])=[CH:13][CH:14]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 685274-Bromobenzyl bromide

Product 1

HCID 1388351-Bromo-4-phenylmethoxybenzeneYield 92.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.07 g (26.8 mmol) of sodium hydride contained at 60% in mineral oil in dry dimethylformamide (80 ml) was added 4.02 g (21.5 mmol) of benzyl alcohol in an atmosphere of argon, and the mixture was allowed to react at 40°-50° C. for 30 min. To the reaction mixture was then added 4.47 g (17.9 mmol) of 4-bromobenzyl bromide, and the mixture was allowed to react at room temperature for 19 hours. To the reaction mixture at 0° C. was added a saturated aqueous solution of ammonium chloride, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography for separation and purification. Elution with dichloromethane-hexane (1:2) yielded 4.61 g (16.6 mmol) of 4-bromophenyl benzyl ether.

Workup

  1. customto react at 40°-50° C. for 30 min
  2. customto react at room temperature for 19 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. concentrationconcentrated under reduced pressure
  6. customThe residue thus obtained
  7. customwas subjected to silica gel column chromatography for separation and purification
  8. washElution with dichloromethane-hexane (1:2)

Sources & evidence

ORD record
ord-37194b7e59d04186b3b02d8941496ea4
Source dataset
uspto-grants-1991_08
Patent number
US05043142

Reaction notes

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