Benzyl Bromide → 4-(3-Benzyloxypropyl)bromobenzene

HRID 1982799Notes

Reaction equation

HRID 1982799 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][OH:13])=[CH:6][CH:5]=1.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[NH4+]>C1C=CC=CC=1>[CH2:14]([O:13][CH2:12][CH2:11][CH2:10][C:7]1[CH:6]=[CH:5][C:4]([Br:3])=[CH:9][CH:8]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 105606143-(4-Bromophenyl)propan-1-ol

Product 1

HCID 219093264-(3-Benzyloxypropyl)bromobenzene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A suspension of sodium hydride (60%, 0.97 g), 3-(4-bromophenyl)-1-propanol (1.0 g) and benzyl bromide (0.69 mL) in benzene (24 mL) was stirred under reflux for 7 hours. After cooling to room temperature, a saturated aqueous ammonium chloride solution (50 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate (100 mL). The organic layer was washed with water (40 mL) and brine (40 mL) 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: hexane/ethyl acetate=20/1) to give 4-(3-benzyloxypropyl)bromobenzene (1.4 g).

Workup

  1. temperatureunder reflux for 7 hours
  2. extractionthe mixture was extracted with ethyl acetate (100 mL)
  3. washThe organic layer was washed with water (40 mL) and brine (40 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-e8c78533f17249429c6555648473159e
Source dataset
uspto-grants-2009_06
Patent number
US07541341B2

Reaction notes

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