Water → 1-Bromo-4-phenylmethoxybenzene

HRID 400240Notes

Reaction equation

HRID 400240 reaction equation
[H-].[Na+].[CH:3]1[C:8]([OH:9])=[CH:7][CH:6]=[C:5]([Br:10])[CH:4]=1.[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>CN(C)C=O>[Br:10][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:3][CH:4]=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

Conditions

Temperature
0 °C

Procedure

15.26 g of sodium hydride at 50% in oil were added at 0° C. to a solution under an inert gas atmosphere of 50 g of p-bromophenol in 320 ml of dimethylformamide and after the mixture was stirred for 30 minutes at 0° C., then 37.7 ml of benzyl bromide were added. The mixture was stirred for 2 hours 30 minutes, allowing the temperature to rise to 20° C., and then the reaction mixture was poured into ice-cooled water. The precipitate was filtered off and dried to obtain 73.35 g of the expected product with an Rf: 0.85 (thin layer chromatography, support: silica, eluant: cyclohexane/ethyl acetate 7/3).

Workup

  1. stirringThe mixture was stirred for 2 hours 30 minutes
  2. customto rise to 20° C.
  3. additionthe reaction mixture was poured into ice-
  4. filtrationThe precipitate was filtered off
  5. customdried

Sources & evidence

ORD record
ord-8a23fc92485242bb93585f415a90e513
Source dataset
uspto-grants-1998_10
Patent number
US05827887

Reaction notes

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