Benzyl Bromide → HCID 58340852、化合物

HRID 72568ノート

反応式

HRID 72568 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-6d5b08f2ccf34f9b8bbb379086f3f137
出典データセット
uspto-grants-2014_09
特許番号
US08828951B2

反応ノート

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