Sodium Carbonate → 2',3'-Difluoro-4'-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-biphenyl-4-carboxylic Acid Ethyl Ester

HRID 48120

반응식

HRID 48120 반응식
[F:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([F:26])([F:25])[C:15]([F:24])([F:23])[C:16]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18])[CH:5]=[CH:4][C:3]=1B(O)O.[CH2:30]([O:32][C:33](=[O:41])[C:34]1[CH:39]=[CH:38][C:37](Br)=[CH:36][CH:35]=1)[CH3:31].C(=O)([O-])[O-].[Na+].[Na+]>O.C1(C)C=CC=CC=1>[CH2:30]([O:32][C:33]([C:34]1[CH:39]=[CH:38][C:37]([C:3]2[CH:4]=[CH:5][C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([F:26])([F:25])[C:15]([F:24])([F:23])[C:16]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18])=[C:7]([F:8])[C:2]=2[F:1])=[CH:36][CH:35]=1)=[O:41])[CH3:31]

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 22043Ethyl 4-bromobenzoateHCID 112708212,3-Difluoro-4-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-phenylboronic Acid

생성물 1

HCID 867593712',3'-Difluoro-4'-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-biphenyl-4-carboxylic Acid Ethyl Ester

시약·촉매·용매 1

HCID 22272177Toluene water용매

실험 절차

A bipsasic solution of 2,3-difluoro-4-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-phenylboronic acid (11A) (1 equi.), 4-bromo-benzoic acid-ethyl ester (12), (1 equi.), sodium carbonate (2.7 equi.), and tetrakis(triphenylphoshine)palladium catalyst (0.01 equi.) in water-toluene (1:1) (2 mL/mmole) was stirred at 100 C temperature for 12 h., cooled to room temperature, extracted with ethyl acetate:hexane(1:1), washed with brine, dried over MgSO4, and concentrated in vacuo. The purification by chromatography on silica gel (5% EtOAc/hexanes) and recrystallization from acetonitrile afforded 2′,3′-difluoro-4′-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-biphenyl-4-carboxylic acid ethyl ester (13A), as a white solid (88%).

후처리

  1. extractionextracted with ethyl acetate:hexane(1:1)
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe purification by chromatography
  6. customon silica gel (5% EtOAc/hexanes) and recrystallization from acetonitrile

출처 및 근거

ORD 기록
ord-c644c6f543cc4565b2d5d1e57d1af403
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06703082B1

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