5-Fluoro-2-nitrophenol → Benzene, 2-[(4,4-difluorocyclohexyl)oxy]-4-fluoro-1-nitro-

HRID 406033노트

반응식

HRID 406033 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.[F:12][C:13]1([F:20])[CH2:18][CH2:17][CH:16](O)[CH2:15][CH2:14]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[F:12][C:13]1([F:20])[CH2:18][CH2:17][CH:16]([O:8][C:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[N+:9]([O-:11])=[O:10])[CH2:15][CH2:14]1

참가 물질

5

반응물 3

HCID 99375-Fluoro-2-nitrophenolHCID 11776TriphenylphosphineHCID 5463004,4-Difluorocyclohexan-1-ol

생성물 1

HCID 58421671Benzene, 2-[(4,4-difluorocyclohexyl)oxy]-4-fluoro-1-nitro-

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

0.213 g DTAD was added into a solution of 5-fluoro-2-nitro-phenol, 0.105 g 4,4-difluorocyclohexanol, 0.25 g triphenylphospine in 2 ml of anhydrous methylene chloride at rt. The reaction mixture was stirred at rt overnight when TLC analysis indicated the consumption of the 5-Fluoro-2-nitro-phenol. The reaction mixture was diluted with methylene chloride (50 ml) and washed with 10% potassium carbonate solution. The aqueous layer was extracted with methylene chloride (2×25 ml) and the combined organics washed with sodium hydrogecarbonate solution (25 ml). The organic layer was passed through a phase separator and concentrated in vacuo. Purification was achieved by silica gel column chromatography (solvent: 100%→1:1 iso-hexane/EtOAc).

후처리

  1. customthe consumption of the 5-Fluoro-2-nitro-phenol
  2. additionThe reaction mixture was diluted with methylene chloride (50 ml)
  3. washwashed with 10% potassium carbonate solution
  4. extractionThe aqueous layer was extracted with methylene chloride (2×25 ml)
  5. washthe combined organics washed with sodium hydrogecarbonate solution (25 ml)
  6. concentrationconcentrated in vacuo
  7. customPurification

출처 및 근거

ORD 기록
ord-d5673a247baa458eac53d82e38a75d94
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754079B2

반응 노트

불러오는 중…