Carbon tetrabromide → alpha-Bromo-o-fluorotoluene

HRID 2264836Notes

Reaction equation

HRID 2264836 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:30]>C(Cl)Cl>[Br:30][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 679692-Fluorobenzylic alcohol

Product 1

HCID 67968alpha-Bromo-o-fluorotolueneYield 93.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-fluorophenyl)methanol (Aldrich, 10.0 g, 79.3 mmol) and triphenylphosphine (29.1 g, 111 mmol) in DCM was added CBr4 (31.6 g, 95.2 mmol) in small portions at 0° C. The mixture was stirred for 2 h at room temperature. The solvent was evaporated and the residue purified via flash chromatography (cyclohexanes:ethyl acetate 95:5) to give the title compound (14 g, 93%). 1H NMR (400 MHz, CDCl3) δ (ppm): 7.42 (t, 1H), 7.36-7.28 (m, 1H), 7.17-7.07 (m, 2H), 4.55 (s, 2H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified via flash chromatography (cyclohexanes:ethyl acetate 95:5)

Sources & evidence

ORD record
ord-caaf57c22f2241ae97db3a59e7c7d2af
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

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