Sodium Carbonate → Methyl 2-(3-methyl-4-fluorophenyl)-5-fluorobenzoate

HRID 1460364노트

반응식

HRID 1460364 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][C:3]=1[CH3:11].Br[C:13]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16].C(=O)([O-])[O-].[Na+].[Na+].[OH-].[NH4+]>O.C(O)C.C1(C)C=CC=CC=1>[CH3:11][C:3]1[CH:4]=[C:5]([C:13]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:14]=2[C:15]([O:17][CH3:18])=[O:16])[CH:6]=[CH:7][C:2]=1[F:1]

참가 물질

8

반응물 4

HCID 10340Sodium Carbonate2회HCID 14923Ammonium HydroxideHCID 138875Benzoic acid, 2-bromo-5-fluoro-, methyl esterHCID 2774580(4-Fluoro-3-methylphenyl)boronic acid

생성물 1

HCID 15037296Methyl 2-(3-methyl-4-fluorophenyl)-5-fluorobenzoate수율 98.7%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 1140Toluene용매

실험 절차

A mixture of 4-fluoro-3-methylphenylboronic acid (6.5 g, 42.5 mmol), methyl 2-bromo-5-fluorobenzoate (10.0 g, 42.9 mmol), tetrakis (triphenylphospine) palladium(0) (1.0 g, 0.87 mmol, 0.2 eq), toluene (100 mL), 2M aqueous sodium carbonate (50 mL) and ethanol (25 mL) was refluxed for 9 h. The reaction mixture was then poured into 50 mL each of concentrated ammonium hydroxide, 2M aqueous sodium carbonate, and water, the organic phase was separated, and the aqueous was extracted with ethyl acetate. The combined organics were washed with brine, dried over MgSO4, and concentrated to leave an oil which was chromatographed on silica gel using hexane to provide 11 g (98%) of the ester.

후처리

  1. temperaturewas refluxed for 9 h
  2. customthe organic phase was separated
  3. extractionthe aqueous was extracted with ethyl acetate
  4. washThe combined organics were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto leave an oil which
  8. customwas chromatographed on silica gel

출처 및 근거

ORD 기록
ord-d58dfe5feaa74d62a802ffa05488e10c
출처 데이터셋
uspto-grants-1991_12
특허 번호
US05070100

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