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

HRID 1640146ノート

反応式

HRID 1640146 の反応式
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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-63466416da5b4ec0a31c39667e5b3913
出典データセット
uspto-grants-2012_02
特許番号
US08110687B2

反応ノート

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