Water → 1-Bromo-4-phenylmethoxybenzene

HRID 840403Notes

Reaction equation

HRID 840403 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>CN(C)C=O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 78084-BromophenolHCID 24758Sodium hydride

Product 1

HCID 1388351-Bromo-4-phenylmethoxybenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

15.26 g of sodium hydride at 50% in oil is added at 0° C. to a solution under inert gas of 50 g of parabromophenol in 320 ml of dimethylformamide (DMF), agitation is carried out for 30 minutes at 0° C., then 37.7 ml of benzyl bromide is added. Agitation is carried out for 2 hours 30 minutes while allowing the temperature to rise to 20° C., then the reaction mixture is poured into ice-cooled water, the precipitate is filtered, and dried, 73.35 g of expected product is obtained. Rf: 0.85 (thin layer chromatography, support: silica, eluant: cyclohexane/ethyl acetate 7/3).

Workup

  1. waitAgitation is carried out for 2 hours 30 minutes
  2. customto rise to 20° C.
  3. additionthe reaction mixture is poured into ice-
  4. filtrationthe precipitate is filtered
  5. customdried

Sources & evidence

ORD record
ord-a2f8c9a533c249c6a9dbf79e5e580a77
Source dataset
uspto-grants-2002_04
Patent number
US06365775B1

Reaction notes

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