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Sodium Carbonate → 3-(2-Fluorophenyl)-5-nitrobenzoic acid

HRID 1726385
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HRID 1726385 반응식
Br[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6].[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>C(COC)OC.CCO.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[N+:11]([C:9]1[CH:8]=[C:4]([CH:3]=[C:2]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[F:14])[CH:10]=1)[C:5]([OH:7])=[O:6])([O-:13])=[O:12]
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참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 2393363-Bromo-5-nitrobenzoic acidHCID 27343542-Fluorophenylboronic acid

생성물 1

HCID 463130863-(2-Fluorophenyl)-5-nitrobenzoic acid수율 83%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매
HCID 702
Ethanol
용매
HCID 80711,2-Dimethoxyethane용매

실험 절차

To a solution of 3-bromo-5-nitro benzoic acid (1 g, 4.06 mmol) and 2-fluoro-phenyl boronic acid (569 mg, 4.06 mmol) in dimethoxyethane (20 ml) and EtOH (1 ml) was added Na2CO3 (7 ml saturated solution) and palladium tetrakis(triphenylphosphine) (94 mg, 0.08 mmol). The mixture was heated at reflux for 4 h and then stirred at RT for 16 h. The grey precipitate that formed was filtered off and washed with CH2Cl2. The filtrate was evaporated, affording 3-nitro-5-(2-fluorophenyl)benzoic acid (intermediate XXXIVj, 880 mg, 83% yield) as a white solid. M+=262.

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 4 h
  3. customThe grey precipitate that formed
  4. filtrationwas filtered off
  5. washwashed with CH2Cl2
  6. customThe filtrate was evaporated

출처 및 근거

ORD 기록
ord-5a0d977cf999493185937818ae8e4ded
출처 데이터셋
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07491821B2

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