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

HRID 1295955ノート

反応式

HRID 1295955 の反応式
[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]

参加物

6

反応物 3

HCID 3283Diethyl EtherHCID 67184N-bromobutanimideHCID 22929663HCID 22929663、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-41ac5f6af2d74d22af3ed315df5b9426
出典データセット
uspto-grants-2007_07
特許番号
US07244730B2

反応ノート

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