Pyridine → 4-(Benzyloxy)-1-(bromomethyl)-2-fluorobenzene

HRID 898661Notes

Reaction equation

HRID 898661 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]O)=[C:11]([F:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.P(Br)(Br)[Br:25]>C(OCC)C.O>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][Br:25])=[C:11]([F:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 24614Phosphorus tribromideHCID 121369904-Benzyloxy-2-fluorobenzyl alcohol2×

Product 1

HCID 158958914-(Benzyloxy)-1-(bromomethyl)-2-fluorobenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A stirred, cooled (ice bath) solution of 4-benzyloxy-2-fluoro-benzyl alcohol (Compound 9, 15 g, 64.6 mmol) in anhydrous diethyl ether (100 mL) was treated with pyridine (5.75 mL, 71.1 mmol) followed by phosphorus tribromide (6.13 mL, 64.6 mmol). After 90 min. the reaction mixture was diluted with water and extracted with diethyl ether (×2). The combined organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title product as an oil that solidified on standing (18 g, 89.5%).

Workup

  1. extractionextracted with diethyl ether (×2)
  2. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-6be6eb9fae8b4fe1967b7c880d3acb12
Source dataset
uspto-grants-2008_04
Patent number
US07351737B2

Reaction notes

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