Pyridine → 1-(Bromomethyl)-4-(4-fluorophenoxy)benzene

HRID 1741005Notes

Reaction equation

HRID 1741005 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([CH2:11]O)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.P(Br)(Br)[Br:24]>C1C=CC=CC=1.O>[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([CH2:11][Br:24])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 24614Phosphorus tribromideHCID 22293127[4-(4-Fluorophenoxy)phenyl]methanol

Product 1

HCID 222626301-(Bromomethyl)-4-(4-fluorophenoxy)benzeneYield 192.4%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 962WaterSolvent

Procedure

4-(4-Fluorophenoxy)benzyl alcohol (1.92 g, 8.80 mmol) and 0.2 ml of pyridine was dissolved in 25 ml of benzene and cooled in cold water. Phosphorus tribromide (1.19 g, 4.40 mmol) in 10 ml of benzene was added dropwise and the reaction was stirred 30 minutes and allowed to warm to room temperature. The solvent was evaporated and the residue was carefully quenched with saturated sodium bicarbonate solution. After dilution with water, the mixture was extracted twice with diethyl ether. The organic extracts were washed with saturated sodium bicarbonate solution and then with brine, dried over MgSO4, and concentrated to afford 2.38 g (96%) of the subtitle compound.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was carefully quenched with saturated sodium bicarbonate solution
  3. extractionAfter dilution with water, the mixture was extracted twice with diethyl ether
  4. washThe organic extracts were washed with saturated sodium bicarbonate solution
  5. dry with materialwith brine, dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8cfffd63b7194aeaa6e969296fc1cd52
Source dataset
uspto-grants-1999_10
Patent number
US05972972

Reaction notes

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