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

HRID 56255노트

반응식

HRID 56255 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-f607e72a2b3a4f3a997b4dde90475ebc
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434695B2

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