Carbon tetrabromide → 1-(Bromomethyl)-3-(2-fluoroethoxy)benzene

HRID 1803814Notes

Reaction equation

HRID 1803814 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:20]([Br:24])(Br)(Br)Br.[F:25][CH2:26][CH2:27][O:28][C:29]1[CH:30]=[C:31](CO)[CH:32]=[CH:33][CH:34]=1>C(Cl)Cl>[Br:24][CH2:20][C:33]1[CH:32]=[CH:31][CH:30]=[C:29]([O:28][CH2:27][CH2:26][F:25])[CH:34]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 53719951(3-(2-Fluoroethoxy)phenyl)methanol

Product 1

HCID 156714111-(Bromomethyl)-3-(2-fluoroethoxy)benzeneYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

PPh3 (3.08 g, 11.8 mmol) and CBr4 (2.93 g, 8.82 mmol) were added to a solution of 37 (1.00 g, 5.88 mmol) in DCM (20 mL) under nitrogen and stirred at room temperature for 1 h. The reaction mixture was filtered, concentrated and chromatographed to isolate the 49 as a colorless solid (0.85 g, 62% yield).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customchromatographed

Sources & evidence

ORD record
ord-d57579141b894028924833d479be325f
Source dataset
uspto-grants-2013_01
Patent number
US08354092B2

Reaction notes

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