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Dimethylformamide → 3,5-Difluoro-4-(hydroxymethyl)benzonitrile

HRID 2404342
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HRID 2404342 반응식
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH2:9][OH:10])=[C:4]([F:11])[CH:3]=1.[CH3:12][N:13](C=O)C>C(Cl)Cl.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.[C-]#N.[Zn+2].[C-]#N>[F:11][C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([F:8])[C:5]=1[CH2:9][OH:10])[C:12]#[N:13]
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참가 물질

7

반응물 2

HCID 6228DimethylformamideHCID 27733034-Bromo-2,6-difluorobenzyl alcohol

생성물 1

HCID 469414123,5-Difluoro-4-(hydroxymethyl)benzonitrile

시약·촉매·용매 4

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 962
Water
용매
HCID 6344Dichloromethane용매

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온도
90 °C

실험 절차

A mixture of (4-bromo-2,6-difluorophenyl)methanol (1.12 g, 5.0 mmol), Pd(PPh3)4 (323 mg, 0.28 mmol) and zinc cyanide (587 mg, 5.0 mmol) was prepared in DMF (7 mL) under nitrogen atmosphere and heated at 90° C. for 18 hours. The mixture was diluted with DCM and water. The organic phase was passed through a hydrophobic frit and the solvent evaporated in vacuo. The residue was purified by flash chromatography (silica, iso-hexane/EtOAc) to afford the title compound. 1H NMR (CDCl3, 400 MHz) δ 7.28-7.21 (2H, m), 4.83 (2H, d, J=6.7 Hz), 1.95 (1H, t, J=6.7 Hz).

후처리

  1. customthe solvent evaporated in vacuo
  2. customThe residue was purified by flash chromatography (silica, iso-hexane/EtOAc)

출처 및 근거

ORD 기록
ord-9e39a18d94fe42d9bc218ac2385947fb
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08802704B2

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