Water → 1-(2-(Benzyloxy)ethyl)-4-bromobenzene

HRID 2354283Notes

Reaction equation

HRID 2354283 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>CN(C)C=O>[CH2:13]([O:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 728512-(4-Bromophenyl)ethanol

Product 1

HCID 219093031-(2-(Benzyloxy)ethyl)-4-bromobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-bromophenyl)ethanol (1.0 g) in N,N-dimethylformamide (25 mL) was added 55% sodium hydride (0.26 g) under ice-cooling, and the mixture was stirred at the same temperature for 15 minutes. To this mixture was added benzyl bromide (0.77 mL) at the same temperature, and the mixture was stirred at the same temperature for 15 minutes, and stirred at room temperature for 30 minutes. The reaction mixture was poured into water, and the resulting mixture was extracted with diethyl ether. The extract was washed with water and brine successively, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane-n-hexane/ethyl acetate=20/1) to give 1-[2-(benzyloxy)ethyl]-4-bromobenzene (1.35 g). The title compound was prepared in a similar manner to that described in Step 2 of Reference Example 46 using this material instead of 1-bromo-2-fluoro-4-methoxybenzene.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at the same temperature for 15 minutes
  3. stirringstirred at room temperature for 30 minutes
  4. extractionthe resulting mixture was extracted with diethyl ether
  5. washThe extract was washed with water and brine successively
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane-n-hexane/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-d0dec30b08504739b6e24d7b594fbbf0
Source dataset
uspto-grants-2010_07
Patent number
US07750145B2

Reaction notes

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