Dimethylformamide → Methyl 3-cyano-5-(trifluoromethyl)benzoate

HRID 1640146노트

반응식

HRID 1640146 반응식
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:16][N:17](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([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>[C:16]([C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])#[N:17]

참가 물질

5

반응물 2

HCID 6228DimethylformamideHCID 18942156Methyl 3-bromo-5-(trifluoromethyl)benzoate

생성물 1

HCID 58902345Methyl 3-cyano-5-(trifluoromethyl)benzoate수율 64%

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매

실험 절차

A mixture of methyl 3-bromo-5-(trifluoromethyl)benzoate (5.10 g, 0.0180 mol), zinc cyanide (1.26 g, 0.0107 mol) and tetrakis(triphenylphosphine)palladium(0) (0.910 g, 0.000787 mol) in DMF (50 mL) was subjected to MWI for 20 min at 230° C. The solvent was evaporated and the residue was suspended in EtOAc. The organic solution was and washed with 1N HCl, water and brine, dried and concentrated. The residue was purified by column chromatography to give methyl 3-cyano-5-(trifluoromethyl)benzoate (2.67 g, 64%) as white solid. 1H NMR (400 MHz, CDCl3) δ: 8.50-8.52 (m, 2H), 8.09 (m, 1H), and 4.03 (s, 3H).

후처리

  1. customThe solvent was evaporated
  2. washwashed with 1N HCl, water and brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-63466416da5b4ec0a31c39667e5b3913
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08110687B2

반응 노트

불러오는 중…