Benzyl Bromide → 4-(3-Benzyloxypropyl)bromobenzene

HRID 2375133Notes

Reaction equation

HRID 2375133 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 for 7 hours under reflux. After cooling to ambient 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
  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-b7ac4fd27b1e45c5a1e80a0f280b7e80
Source dataset
uspto-grants-2008_12
Patent number
US07465712B2

Reaction notes

Loading…