Boron trifluoride etherate → 1-[6-(5-Bromo-2-chloro-benzyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone

HRID 72572노트

반응식

HRID 72572 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:26])=[C:6]([CH:25]=1)[C:7]([C:9]1[CH:10]=[CH:11][C:12]2[O:17][CH2:16][CH2:15][N:14]([C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[C:13]=2[CH:24]=1)=O.B(F)(F)F.CCOCC.[SiH](CC)(CC)CC>ClCCCl.CC#N>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:26])=[C:6]([CH:25]=1)[CH2:7][C:9]1[CH:10]=[CH:11][C:12]2[O:17][CH2:16][CH2:15][N:14]([C:18](=[O:23])[C:19]([F:21])([F:22])[F:20])[C:13]=2[CH:24]=1

참가 물질

5

반응물 3

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 866551971-[6-(5-Bromo-2-chloro-benzoyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone

생성물 1

HCID 583408561-[6-(5-Bromo-2-chloro-benzyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone수율 85.9%

시약·촉매·용매 1

HCID 22402149Acetonitrile 1,2-dichloroethane용매

실험 절차

To a stirred solution of 1-[6-(5-bromo-2-chloro-benzoyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone (36 g, 80.35 mmol) in 1,2-dichloroethane:MeCN 1:2 (180 mL) was added BF3.OEt2 (13.2 mL, 104 mmol) and Et3SiH (26.9 mL, 168.7 mmol) at 0° C. The reaction mixture was stirred overnight at room temperature then quenched by the addition of aq. NaHCO3 (˜200 mL). The resulting mixture was extracted with ethyl acetate (3×200 mL), and the combined organic layers were washed with brine (200 mL) and dried over sodium sulfate. Crude product obtained after evaporation of solvent was purified by silica gel column chromatography to furnish 1-[6-(5-bromo-2-chloro-benzyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone (30 g).

후처리

  1. customthen quenched by the addition of aq. NaHCO3 (˜200 mL)
  2. extractionThe resulting mixture was extracted with ethyl acetate (3×200 mL)
  3. washthe combined organic layers were washed with brine (200 mL)
  4. dry with materialdried over sodium sulfate
  5. customCrude product obtained
  6. customafter evaporation of solvent
  7. customwas purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-eddbc94e7c034c62ade11f5f1b6b7749
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828951B2

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