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

HRID 1607440ノート

反応式

HRID 1607440 の反応式
[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]

参加物

8

反応物 4

HCID 10340Sodium Carbonate2 回HCID 14923Ammonium HydroxideHCID 138875Benzoic acid, 2-bromo-5-fluoro-, methyl esterHCID 2774580(4-Fluoro-3-methylphenyl)boronic acid

生成物 1

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

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

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(O) (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.

後処理

  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

出典と根拠

ORDレコード
ord-5c9da5a72e654323a9395345aae35c30
出典データセット
uspto-grants-1989_09
特許番号
US04864028

反応ノート

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