Water → Benzenemethanol, 4-(difluoromethoxy)-2,6-difluoro-

HRID 1484683노트

반응식

HRID 1484683 반응식
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[C:6]([F:10])[C:7]=1[CH2:8][OH:9].Cl[C:13]([F:18])([F:17])C([O-])=O.[Na+].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C.C(OCC)(=O)C>[F:17][CH:13]([F:18])[O:11][C:4]1[CH:3]=[C:2]([F:1])[C:7]([CH2:8][OH:9])=[C:6]([F:10])[CH:5]=1

참가 물질

7

반응물 4

HCID 962Water2회HCID 10796Cesium carbonateHCID 2734985Sodium chlorodifluoroacetateHCID 222199753,5-Difluoro-4-(hydroxymethyl)phenol

생성물 1

HCID 69140944Benzenemethanol, 4-(difluoromethoxy)-2,6-difluoro-수율 56%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

500 mg 3,5-difluoro-4-(hydroxymethyl)phenol (3.12 mmol, 1.0 eq.) were dissolved in DMF. 523 mg sodium chloro(difluoro)acetate (3.44 mmol, 1.1 eq.), 1.22 g cesium carbonate (3.75 mmo, 1.2 eq) and 0.20 mL water (10.9 mmol, 3.5 eq.) were added. The reaction mixture was stirred at 100° C. over night. The reaction mixture was divided between water and ethyl acetate. The aqueous layer was washed twice with ethyl acetate. The combined organic layers were washed with brine, dried over a silicon filter and concentrated in vacuo. The crude product was purified by flash chromatography to provide 161 mg (0.69 mmol, 22%) of the 56% pure target compound.

후처리

  1. washThe aqueous layer was washed twice with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. customdried over a silicon
  4. filtrationfilter
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography

출처 및 근거

ORD 기록
ord-ccdc2f7392d948c583bacedff73d2af3
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422268B2

반응 노트

불러오는 중…