Hydrochloric Acid → 1-(2-Fluorobiphenyl-4-yl)cyclopropanecarboxylic acid

HRID 1879435ノート

反応式

HRID 1879435 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([OH:13])=[O:12])[CH2:10][CH2:9]2)=[CH:4][C:3]=1[F:14].[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+].Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:14][C:3]1[CH:4]=[C:5]([C:8]2([C:11]([OH:13])=[O:12])[CH2:10][CH2:9]2)[CH:6]=[CH:7][C:2]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 116518041-(4-Bromo-3-fluorophenyl)cyclopropane-1-carboxylic acid

生成物 1

HCID 117086541-(2-Fluorobiphenyl-4-yl)cyclopropanecarboxylic acid収率 214%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 167845palladium(II) acetate触媒

反応条件

温度
130 °C

実験手順

800 mg (3.1 mmoles) of 4-bromo-3-fluorophenylcyclopropanecarboxylic acid and 650 mg (3.4 mmoles) of phenylboronic acid are suspended in 8 ml of a 2M K2CO3 aqueous solution. The mixture is added with tetrabutylammonium bromide (960 mg, 3 mmoles) and palladium(II) acetate (40 mg, 0.18 mmoles) and heated at 130° C. in a closed reactor for 30 minutes. After cooling at room temperature, the mixture is added with 2M HCl (25 ml) and extracted with ethyl acetate. The organic phase is washed with 1N HCl, then with brine, finally dried and concentrated under vacuum to give an oil (1.7 g), which is crystallized from isopropyl ether-hexane to afford the product as a white solid (0.2 g).

後処理

  1. temperatureAfter cooling at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with 1N HCl
  4. dry with materialwith brine, finally dried
  5. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-a118b428a2f44b9cbf892e93f7e34d88
出典データセット
uspto-grants-2012_11
特許番号
US08314268B2

反応ノート

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