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 1874893노트

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HRID 1874893 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매

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온도
120 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f54c6704b06342e9827deca19e35d9e7
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

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