Water → 1-(3-Bromopropyl)-4-fluorobenzene

HRID 1093343Notes

Reaction equation

HRID 1093343 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10]O)=[CH:4][CH:3]=1.P(Br)(Br)[Br:13].O>C(OCC)C>[Br:13][CH2:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 137472413-(4-Fluorophenyl)propan-1-ol

Product 1

HCID 147371331-(3-Bromopropyl)-4-fluorobenzene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Compound 20-1 (9.39 g) was dissolved in diethyl ether (100 ml), phosphorus tribromide (8.58 ml) was added under ice-cooling, and the mixture was stirred under ice-cooling for 3.5 hr. To the reaction mixture was slowly added water, and the mixture was extracted with diethyl ether. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the object product (4.93 g) as a pale-yellow oil.

Workup

  1. temperaturecooling
  2. temperaturecooling for 3.5 hr
  3. extractionthe mixture was extracted with diethyl ether
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6b5bd590909e4dbe9e10959ba0cdaf86
Source dataset
uspto-grants-2012_03
Patent number
US08129361B2

Reaction notes

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