Sodium Carbonate → 4-Fluoro-3'-methoxy-3-nitrobiphenyl

HRID 1019138

반응식

HRID 1019138 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1.Br[C:13]1[CH:14]=[CH:15][C:16]([F:22])=[C:17]([N+:19]([O-:21])=[O:20])[CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.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>[F:22][C:16]1[CH:15]=[CH:14][C:13]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:18][C:17]=1[N+:19]([O-:21])=[O:20]

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

생성물 1

HCID 104907024-Fluoro-3'-methoxy-3-nitrobiphenyl수율 77%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

Tetrakis(triphenylphosphine)palladium (0.8 g) was added to a mixture of 5 g 3-methoxyphenylboronic acid, 5 g 5-bromo-2-fluoronitrobenzene and 11 mL of 2 M sodium carbonate solution in 100 mL of toluene. The mixture was refluxed for 2 hours, diluted with water and extracted with ethyl acetate. The ethyl acetate was washed with saturated sodium bicarbonate and brine and then dried and concentrated to give an oily solid. The solid was chromatographed on silica gel (ethyl acetate:hexane (1:6)) to give 4.3 g (77% yield) of 4-fluoro-3′-methoxy-3- nitrobiphenyl.

후처리

  1. temperatureThe mixture was refluxed for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate was washed with saturated sodium bicarbonate and brine
  4. customdried
  5. concentrationconcentrated
  6. customto give an oily solid
  7. customThe solid was chromatographed on silica gel (ethyl acetate:hexane (1:6))

출처 및 근거

ORD 기록
ord-8342122c5d8f4d40ae282889278714f3
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06486185B1

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