Benzyl Bromide → HCID 58340852、化合物

HRID 1258812ノート

反応式

HRID 1258812 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:19])=[C:6]([CH:18]=1)[CH2:7][C:8]1[CH:9]=[CH:10][C:11]2[O:16][CH2:15][CH2:14][NH:13][C:12]=2[CH:17]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C>[CH2:26]([N:13]1[C:12]2[CH:17]=[C:8]([CH2:7][C:6]3[CH:18]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=3[Cl:19])[CH:9]=[CH:10][C:11]=2[O:16][CH2:15][CH2:14]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 67115789HCID 67115789、化合物

生成物 1

HCID 58340852HCID 58340852、化合物収率 69%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

To a stirred solution of 6-(5-bromo-2-chloro-benzyl)-3,4-dihydro-2H-benzo[1,4]oxazine (8.0 g, 23.66 mmol) in DMF (35 mL) was added potassium carbonate (6.53 g, 36.0 mmol), benzyl bromide (4.33 mL, 35.50 mmol) and heated to 50° C. for 8 h. Reaction mixture was cooled to room temperature, quenched by the addition of water (50 mL), extracted with ethyl acetate (3×20 mL). The organic layer was washed with water (50 mL), brine (50 mL), dried over sodium sulfate, concentrated and purified by silica gel column chromatography to furnish 4-benzyl-6-(5-bromo-2-chloro-benzyl)-3,4-dihydro-2H-benzo[1,4]oxazine (7.0 g).

後処理

  1. customReaction mixture
  2. temperaturewas cooled to room temperature
  3. customquenched by the addition of water (50 mL)
  4. extractionextracted with ethyl acetate (3×20 mL)
  5. washThe organic layer was washed with water (50 mL), brine (50 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. custompurified by silica gel column chromatography

出典と根拠

ORDレコード
ord-c5d15fb6dcfa4c1c99bc3eb458a95f5a
出典データセット
uspto-grants-2013_06
特許番号
US08466114B2

反応ノート

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