Benzyl Bromide → HCID 58340852, 화합물

HRID 1258818노트

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HRID 1258818 반응식
[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

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 67115789HCID 67115789, 화합물

생성물 1

HCID 58340852HCID 58340852, 화합물수율 69%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

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, 47.3 mmol), and benzyl bromide (4.33 mL, 35.50 mmol). The reaction mixture was heated to 60° C. for 8 h, then cooled to room temperature and quenched by the addition of ice-cold water (50 mL). The resulting mixture was extracted with ethyl acetate (3×30 mL), and the combined organic layers were washed with water (50 mL) and brine (50 mL), then dried over sodium sulfate. The sodium sulfate was filtered off and the filtrate was concentrated to crude product which was 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).

후처리

  1. temperaturecooled to room temperature
  2. customquenched by the addition of ice-cold water (50 mL)
  3. extractionThe resulting mixture was extracted with ethyl acetate (3×30 mL)
  4. washthe combined organic layers were washed with water (50 mL) and brine (50 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationThe sodium sulfate was filtered off
  7. concentrationthe filtrate was concentrated to crude product which
  8. customwas purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-9e39ef0aaa1f47a285a559e5ad4c25e0
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466114B2

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