Triphenylphosphine → 1-(Bromomethyl)-2-fluoro-4-nitrobenzene

HRID 1842940Notes

Reaction equation

HRID 1842940 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C(=O)N([Br:39])C(=O)C1>C(Cl)Cl>[Br:39][CH2:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 17981733(2-Fluoro-4-nitrophenyl)methanol

Product 1

HCID 218861321-(Bromomethyl)-2-fluoro-4-nitrobenzeneYield 85.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) and stirred solution of DCM (100 mL) containing (2-fluoro-4-nitrophenyl)methanol (9 g, 52.6 mmol, 1 eq), triphenylphosphine (16.5 g, 63.1 mmol, 1.2 eq) was added followed by addition of NBS (11.24 g, 63.1 mmol, 1.2 eq), the mixture was allowed to warm to RT and stirred for 2 h. The DCM was evaporated under reduced pressure and the residue was purified by CC using PE/EtOAc (9:1) as eluent to get 1-(bromomethyl)-2-fluoro-4-nitrobenzene (10.50 g, 85%; TLC system: PE/EtOAc (7:3), Rf: 0.6).

Workup

  1. additionwas added
  2. temperatureto warm to RT
  3. customThe DCM was evaporated under reduced pressure
  4. customthe residue was purified by CC

Sources & evidence

ORD record
ord-74105034320f4b23a142c0e2b37820ad
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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