Triphenylphosphine → 3'-(Bromomethyl)-5'-(trifluoromethyl)biphenyl-4-carbonitrile

HRID 391371

Reaction equation

HRID 391371 reaction equation
[Br:1]N1C(=O)CCC1=O.O[CH2:10][C:11]1[CH:12]=[C:13]([C:21]2[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=2)[CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Br:1][CH2:10][C:11]1[CH:12]=[C:13]([C:21]2[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=2)[CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 589936723'-(Hydroxymethyl)-5'-(trifluoromethyl)biphenyl-4-carbonitrile

Product 1

HCID 589934903'-(Bromomethyl)-5'-(trifluoromethyl)biphenyl-4-carbonitrileYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-bromosuccinimide (2.24 g, 12.6 mmol) was added to a 0° C. solution of 3′-(hydroxymethyl)-5′-(trifluoromethyl)biphenyl-4-carbonitrile (1.66 g, 6.0 mmol) and triphenylphosphine (3.14 g, 12.0 mmol) in THF (100 mL). The reaction was warmed to ambient temperature and stirred for 18 hours. The solvent was evaporated and the residue was purified by chromatography on SiO2 with a gradient of ethyl acetate/hexanes of 5% to 40%. The product 3′-(bromomethyl)-5′-(trifluoromethyl)biphenyl-4-carbonitrile (1.30 g, 64%) was obtained as a white solid. 1H-NMR (CDCl3, 400 MHz) δ 7.65-7.80 (m, 7H), 4.56 (s, 2H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by chromatography on SiO2 with a gradient of ethyl acetate/hexanes of 5% to 40%

Sources & evidence

ORD record
ord-1b24b27c1ecc4ddebe9a66406204f0cb
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Linked notes

Loading…