Bromine → 4-bromo-N-(3-fluoro-4-morpholinophenyl)-3-oxobutanamide

HRID 56255ノート

反応式

HRID 56255 の反応式
[F:1][C:2]1[CH:3]=[C:4]([NH:14][C:15](=[O:20])[CH2:16][C:17](=[O:19])[CH3:18])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[Br:21]Br>CC(O)=O>[Br:21][CH2:18][C:17](=[O:19])[CH2:16][C:15]([NH:14][C:4]1[CH:5]=[CH:6][C:7]([N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)=[C:2]([F:1])[CH:3]=1)=[O:20]

参加物

4

反応物 2

HCID 24408BromineHCID 90023295N-(3-fluoro-4-morpholinophenyl)-3-oxobutanamide

生成物 1

HCID 900232464-bromo-N-(3-fluoro-4-morpholinophenyl)-3-oxobutanamide収率 47%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a solution of N-(3-fluoro-4-morpholinophenyl)-3-oxobutanamide (11.2 g, 40.0 mmol) and AcOH (100 mL) under N2 was added Br2 (2.4 mL) at rt. At end of addition, the mixture was stirred further at rt for 24 h. The mixture was then concentrated in vacuo and 40 mL of water was added. The resulting mixture was extracted with EtOAc (30 mL×4). The combined organic phases were washed with brine (40 mL×3), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1) to give the title compound as a yellow solid (6.80 g, 47%).

後処理

  1. additionAt end of addition
  2. concentrationThe mixture was then concentrated in vacuo and 40 mL of water
  3. additionwas added
  4. extractionThe resulting mixture was extracted with EtOAc (30 mL×4)
  5. washThe combined organic phases were washed with brine (40 mL×3)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1)

出典と根拠

ORDレコード
ord-f607e72a2b3a4f3a997b4dde90475ebc
出典データセット
uspto-grants-2016_09
特許番号
US09434695B2

反応ノート

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