Diethyl Ether → 2-Bromo-1-(3-tert-butyl-4-methoxy-5-morpholinophenyl)ethanone

HRID 1295955노트

반응식

HRID 1295955 반응식
[C:1]([C:5]1[CH:6]=[C:7]([C:19](=[O:21])[CH3:20])[CH:8]=[C:9]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:10]=1[O:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].[Br:22]N1C(=O)CCC1=O.CCOCC>O1CCCC1.C(N(CC)CC)C>[Br:22][CH2:20][C:19]([C:7]1[CH:8]=[C:9]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[C:10]([O:11][CH3:12])=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=1)=[O:21]

참가 물질

6

반응물 3

HCID 3283Diethyl EtherHCID 67184N-bromobutanimideHCID 22929663HCID 22929663, 화합물

생성물 1

HCID 229297822-Bromo-1-(3-tert-butyl-4-methoxy-5-morpholinophenyl)ethanone수율 34.9%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매

실험 절차

After dissolving the 1-[3-(tert-butyl)-4-methoxy-5-morpholinophenyl]-1-ethanone (76 g) in tetrahydrofuran (600 ml), triethylamine (110 ml) and tert-butyl dimethylsilyltrifluoromethanesulfonate (75 ml) was added dropwise while cooling on ice. The reaction mixture was stirred for 30 minutes while cooling on ice and then N-bromosuccinimide (70 g) was gradually added. After stirring the reaction mixture for 30 minutes, 2 l of ether was added and the mixture was washed twice with water. The organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (33.7 g) as light yellow crystals.

후처리

  1. additionwas added dropwise
  2. temperaturewhile cooling on ice
  3. temperaturewhile cooling on ice
  4. stirringAfter stirring the reaction mixture for 30 minutes
  5. washthe mixture was washed twice with water
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

출처 및 근거

ORD 기록
ord-41ac5f6af2d74d22af3ed315df5b9426
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07244730B2

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