3-Bromotoluene → 2-(3-Methylphenyl)benzonitrile

HRID 743892

반응식

HRID 743892 반응식
Br[C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1.[Li]C(C)(C)C.Br[C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[C:17]#[N:18]>[Cl-].[Cl-].[Zn+2].C1C=CC([P]([Ni]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:8][C:4]1[CH:3]=[C:2]([C:15]2[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=2[C:17]#[N:18])[CH:7]=[CH:6][CH:5]=1

참가 물질

6

반응물 3

HCID 115603-BromotolueneHCID 162722-BromobenzonitrileHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 13942432-(3-Methylphenyl)benzonitrile수율 46.7%

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 178420538HCID 178420538, 화합물촉매

실험 절차

3-Bromotoluene (17.5 mmoles, 3.0 g) was reacted with t-BuLi(19.3 mmoles) and ZnCl2 (19 3 moles, 2.62 g) followed by a Ni(PPh3)4 coupling to 2-bromobenzonitrile (17.5 mmole, 3.2 g) as in Preparation 1. The intermediate was purified by chromatography over silica gel eluted with 20% ether in hexane to yield 1.58 g of 2-(3-methylphenyl)-benzonitrile (MS)

후처리

  1. customThe intermediate was purified by chromatography over silica gel
  2. washeluted with 20% ether in hexane

출처 및 근거

ORD 기록
ord-0f05d856683b4c7bb91138ff7d823c30
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05556981

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