Sodium Carbonate → Methyl 2-(4-fluorophenyl)-4-methylbenzoate

HRID 1251864ノート

反応式

HRID 1251864 の反応式
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4](OS(C(F)(F)F)(=O)=O)[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[F:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.[Cl-].[Li+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.[Pd].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.C(O)C>[F:26][C:27]1[CH:32]=[CH:31][C:30]([C:4]2[CH:3]=[C:2]([CH3:1])[CH:11]=[CH:10][C:5]=2[C:6]([O:8][CH3:9])=[O:7])=[CH:29][CH:28]=1

参加物

9

反応物 4

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 433294Lithium ChlorideHCID 18474576Methyl 2-trifluoromethylsulfonyloxy-4-methylbenzoate

生成物 1

HCID 18474522Methyl 2-(4-fluorophenyl)-4-methylbenzoate収率 99%

試薬・触媒・溶媒 4

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Tetrakis(triphenylphosphine) palladium (9 g; 7.8 mmol) and ethanol (780 ml) was added to a suspension of methyl 4-methyl-2-trifluoromethanesulphonyloxybenzoate (58 g; 0.195 mol), 2M aqueous solution of sodium carbonate (250 ml; 0.5 mol), 4-fluorophenylboronic acid (30 g ; 0.214 mol) and lithium chloride (16.5 g ; 0.39 mol) in toluene (1.65 ml), under an argon atmosphere, The mixture was refluxed for 4 hours, diluted with ethyl acetate (1 l) and washed with aqueous sodium hydroxide solution 1N (1 l). The organic phase was evaporated and the residue purified by flash column chromatography using ethyl acetatelpetroleum ether (95:5) to give methyl 2-(4-fluorophenyl)-4-methylbenzoate (46.8 g; 99%).

後処理

  1. temperatureThe mixture was refluxed for 4 hours
  2. washwashed with aqueous sodium hydroxide solution 1N (1 l)
  3. customThe organic phase was evaporated
  4. customthe residue purified by flash column chromatography

出典と根拠

ORDレコード
ord-4f4e310c66f74ef989de0ec00154098b
出典データセット
uspto-grants-2002_01
特許番号
US06342765B1

反応ノート

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