N-bromobutanimide → 2-(Bromomethyl)-1-fluoro-4-methoxybenzene

HRID 1522890Notes

Reaction equation

HRID 1522890 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH3:10].C1C(=O)N([Br:18])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:10][C:3]1[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=1[F:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 1375464-Fluoro-3-methylanisole

Product 1

HCID 218916842-(Bromomethyl)-1-fluoro-4-methoxybenzeneYield 95.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 1-fluoro-4-methoxy-2-methylbenzene (2.0 g, 14.29 mmol) in CCl4, NBS (2.55 g, 14.29 mmol) and PhCO3H (80 mg) were added. The reaction mixture was heated at reflux for 2 h, cooled to room temperature, and the solid was filtered off. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (eluting with PE/EA=20/1) to give the target compound (3.0 g) as an oil. 1H NMR (CDCl3): δ 6.97-6.83 (m, 3H), 4.48 (s, 2H), 3.78 (s, 3H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. filtrationthe solid was filtered off
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by silica gel column chromatography (eluting with PE/EA=20/1)

Sources & evidence

ORD record
ord-50a5173d81a141b89045db6bcbbbbe39
Source dataset
uspto-grants-2015_07
Patent number
US09078871B2

Reaction notes

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