Carbon tetrabromide → 3-Bromo-methyl-5-trifluoromethyl-benzonitrile

HRID 604217노트

반응식

HRID 604217 반응식
OC[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:6]#[N:7].[C:15]([Br:19])(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:19][C:15]1[C:4]([CH3:3])=[C:5]([CH:8]=[C:9]([C:11]([F:12])([F:14])[F:13])[CH:10]=1)[C:6]#[N:7]

참가 물질

5

반응물 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 117012213-(Hydroxymethyl)-5-(trifluoromethyl)benzonitrile

생성물 1

HCID 666029993-Bromo-methyl-5-trifluoromethyl-benzonitrile수율 83%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

3-Hydroxymethyl-5-trifluoromethyl-benzonitrile (23.4 g) is dissolved in methylene chloride (230 mL) and thereto is added carbon tetrabromide (42.4 g), followed by an addition of triphenylphosphine (32.0 g) under ice-cooling and the mixture is stirred at the same temperature for 30 minutes. The reaction solution is concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to give 3-bromo-methyl-5-trifluoromethyl-benzonitrile (25.5 g). NMR (CDCl3): 4.51 (2H, s), 7.86 (1H, s), 7.88 (2H, s)

후처리

  1. temperaturecooling
  2. concentrationThe reaction solution is concentrated under reduced pressure
  3. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

출처 및 근거

ORD 기록
ord-f0f9af64c2324477a4db59d9f4b4d8b2
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906517B2

반응 노트

불러오는 중…