Morpholine → 3-Bromo-4-morpholinobenzaldehyde

HRID 48053

반응식

HRID 48053 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1F)[CH:5]=[O:6].[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C([O-])([O-])=O.[K+].[K+]>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)[CH:5]=[O:6]

참가 물질

5

반응물 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 1736043-Bromo-4-fluorobenzaldehyde

생성물 1

HCID 235060203-Bromo-4-morpholinobenzaldehyde수율 58.2%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

Ex-604A) To a pyridine (15 mL) solution of 3-bromo-4-fluorobenzaldehyde (1.0 g, 4.9 mmol) was added morpholine (0.5 mL, 5.7 mmol) and K2CO3 (0.69 g, 5.0 mmol), and the slurry was refluxed for 18 h. The solvent was removed, and the residue was partitioned between ethyl acetate and water. The organic layer was separated, dried (MgSO4) and evaporated to a yellow oil. Purification by flash chromatography on silica gel eluting with 15% ethyl acetate in hexane gave 0.77 g (58%) of the desired 3-bromo-4-(4-morpholinyl)benzaldehyde product as an white solid. 1H NMR (CDCl3) δ3.18 (m, 4H), 3.90 (m, 4H), 7.10 (d, 1H), 7.78 (d, 1H), 8.07 (s, 1H), 9.83 (s, 1H).

후처리

  1. temperaturethe slurry was refluxed for 18 h
  2. customThe solvent was removed
  3. customthe residue was partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. customevaporated to a yellow oil
  7. customPurification by flash chromatography on silica gel eluting with 15% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-b27738df338946dca7450462a9f3cf17
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699898B2

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