3-Fluoroaniline → (4-Fluoro-phenyl)-(3-fluoro-phenylamino)-acetic acid

HRID 1044033

反応式

HRID 1044033 の反応式
Br[CH:2]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].[F:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17]>C(#N)C.CCOC(C)=O>[F:12][C:9]1[CH:10]=[CH:11][C:6]([CH:2]([NH:17][C:16]2[CH:18]=[CH:19][CH:20]=[C:14]([F:13])[CH:15]=2)[C:3]([OH:5])=[O:4])=[CH:7][CH:8]=1

参加物

5

反応物 2

HCID 97423-Fluoroaniline2 回HCID 16217752Bromo(4-fluorophenyl)acetic acid

生成物 1

HCID 54890833(4-Fluoro-phenyl)-(3-fluoro-phenylamino)-acetic acid収率 90.1%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2-bromo-2-(4-fluorophenyl)acetic acid (500 mg, 2.15 mmol) and 3-fluoroaniline (477 mg, 4.29 mmol) in acetonitrile (8 ml) was heated under microwave irradiation at 100° C. for 50 minutes. Then 3-fluoroaniline (238 mg, 2.15 mmol) was added again, and the reaction mixture was heated at 120° C. for 45 minutes in a microwave oven (UPLC-MS monitoring: complete conversion). The organic solution was diluted with EtOAc and was washed with 2N HCl and then with brine. The organic phase was dried over Na2SO4, filtered and the solvent was evaporated to give 2-(4-fluorophenyl)-2-(3-fluorophenylamino)acetic acid (510 mg, 90% yield).

後処理

  1. temperaturethe reaction mixture was heated at 120° C. for 45 minutes in a microwave oven (UPLC-MS monitoring: complete conversion)
  2. washwas washed with 2N HCl
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-00e485c4da9d42d0b1ddd573c2dd10c1
出典データセット
uspto-grants-2013_10
特許番号
US08563577B2

関連ノート

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