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

HRID 391371

반응식

HRID 391371 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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%

출처 및 근거

ORD 기록
ord-1b24b27c1ecc4ddebe9a66406204f0cb
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383821B2

연결된 노트

불러오는 중…