Potassium Bromide → 3-(4'-Fluorobiphenyl-4-yl)propanal

HRID 2410464노트

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HRID 2410464 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16](O)=[O:17])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Br-].[K+].Cl[O-].[Na+].C(=O)(O)[O-].[Na+]>ClCCl.CC1(C)N([O])C(C)(C)CCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH:16]=[O:17])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 253877Potassium BromideHCID 516892Sodium BicarbonateHCID 1393679[1,1'-Biphenyl]-4-propanoicacid, 4'-fluoro-HCID 23665760Sodium Hypochlorite

생성물 1

HCID 867009833-(4'-Fluorobiphenyl-4-yl)propanal

시약·촉매·용매 2

HCID 2724126Tempo촉매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a stirred solution of the compound obtained from step d above (0.7 g) in dichloromethane (10 mL), 2,2,6,6-tetramethylpiperidine N-oxyl (4.74 mg) and potassium bromide (36.05 mg) were added at 0° C. under nitrogen atmosphere. Sodium hypochlorite (0.28 g, 4% solution) was added at pH 8-9 (maintained by adding aqueous sodium bicarbonate solution). The reaction mixture was stirred for 20 minutes at 0° C. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with saturated aqueous sodium bicarbonate solution, water, and brine. The organic layer was dried over anhydrous sodium sulphate, filtered, and concentrated under reduced pressure to afford the title compound (0.55 g).

후처리

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate solution, water, and brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-85f76d7940164c20bcfa6d8e2fab9beb
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08816073B2

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