2-[(3-Bromo-2,5-dichlorophenyl)oxy]-1-chloro-3-fluoro-4-methylbenzene → 2,5-Dichloro-3-[(6-chloro-2-fluoro-3-methylphenyl)oxy]benzonitrile

HRID 1874893ノート

反応式

HRID 1874893 の反応式
Br[C:2]1[C:3]([Cl:19])=[C:4]([O:9][C:10]2[C:15]([F:16])=[C:14]([CH3:17])[CH:13]=[CH:12][C:11]=2[Cl:18])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:20]([Zn]C#N)#[N:21]>CCOC(C)=O.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>[Cl:19][C:3]1[C:4]([O:9][C:10]2[C:11]([Cl:18])=[CH:12][CH:13]=[C:14]([CH3:17])[C:15]=2[F:16])=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[C:20]#[N:21]

参加物

5

反応物 2

HCID 684874142-[(3-Bromo-2,5-dichlorophenyl)oxy]-1-chloro-3-fluoro-4-methylbenzeneHCID 178514179HCID 178514179、化合物

生成物 1

HCID 684840922,5-Dichloro-3-[(6-chloro-2-fluoro-3-methylphenyl)oxy]benzonitrile収率 117.7%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

2-[(3-bromo-2,5-dichlorophenyl)oxy]-1-chloro-3-fluoro-4-methylbenzene (2.0 g, 5.20 mmol) was combined with dicyanozinc (0.305 g, 2.60 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.601 g, 0.520 mmol) and heated at 120° C. for 60 min in a microwave reactor under an inert atmosphere. The reaction mixture was diluted with EtOAc, washed four times with water, dried over MgSO4, filtered and concentrated to dryness. The residue was purified on 120 g silica eluted successively with 100% hexanes followed by 0 to 10% EtOAc/hexanes to give 2,5-dichloro-3-[(6-chloro-2-fluoro-3-methylphenyl)oxy]benzonitrile (1.01 g, 3.06 mmol, 58.7% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.00 (d, J=2.20 Hz, 1H), 7.31-7.47 (m, 2H), 7.24 (d, J=1.83 Hz, 1H), 2.29 (d, J=1.74 Hz, 3H).

後処理

  1. washwashed four times with water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe residue was purified on 120 g silica
  6. washeluted successively with 100% hexanes

出典と根拠

ORDレコード
ord-f54c6704b06342e9827deca19e35d9e7
出典データセット
uspto-grants-2012_11
特許番号
US08304419B2

反応ノート

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