Carbon tetrabromide → 1-(Bromomethyl)-2-fluoro-3-methoxybenzene

HRID 424692Notes

Reaction equation

HRID 424692 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:20][C:21]1[C:26]([O:27][CH3:28])=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:29]O.C(Br)(Br)(Br)[Br:32]>C(Cl)Cl>[Br:32][CH2:29][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]([O:27][CH3:28])[C:21]=1[F:20]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromide2×HCID 11776Triphenylphosphine2×HCID 5935892-Fluoro-3-methoxybenzyl alcohol

Product 1

HCID 269861001-(Bromomethyl)-2-fluoro-3-methoxybenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphenylphosphine (11.1 g) was added to a solution of the subtitle product of step ii) (5.0 g) in DCM (200 ml) followed by the portionwise addition of carbon tetrabromide (14.0 g). The reaction was stirred for 4 h before the addition of further triphenylphosphine (2.0 g) and carbon tetrabromide (2.0 g) and stirring maintained for 1 h. The mixture was concentrated to 30 ml volume and diluted in Et2O (300 ml). The solid precipitate was filtered and washed with Et2O (3×) and the filtrate concentrated in vacuo. The residue was purified by column chromatography (10% Et2O/iso-hexane) to afford the subtitle compound as a clear oil. Yield: 5.2 g.

Workup

  1. temperaturemaintained for 1 h
  2. concentrationThe mixture was concentrated to 30 ml volume
  3. additiondiluted in Et2O (300 ml)
  4. filtrationThe solid precipitate was filtered
  5. washwashed with Et2O (3×)
  6. concentrationthe filtrate concentrated in vacuo
  7. customThe residue was purified by column chromatography (10% Et2O/iso-hexane)

Sources & evidence

ORD record
ord-2e7cac7b36ec4a1a842112a8a8cfd0e4
Source dataset
uspto-grants-2012_01
Patent number
US08106063B2

Reaction notes

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