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Water → 6-Bromo-7-fluoro-2H-1,4-benzoxazin-3(4H)-one

HRID 519227
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HRID 519227 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[C:5]([F:9])=[CH:4][C:3]=1[OH:10].C([O-])([O-])=O.[K+].[K+].Cl[CH2:18][C:19](Cl)=[O:20].O>CN(C=O)C>[Br:8][C:6]1[C:5]([F:9])=[CH:4][C:3]2[O:10][CH2:18][C:19](=[O:20])[NH:1][C:2]=2[CH:7]=1
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참가 물질

6

반응물 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 383722992-Amino-4-bromo-5-fluorophenol

생성물 1

HCID 235743206-Bromo-7-fluoro-2H-1,4-benzoxazin-3(4H)-one수율 90.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매
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온도
80 °C

실험 절차

To a 0° C. mixture of 2-amino-4-bromo-5-fluorophenol (38.0 g, crude from previous step) and K2CO3 (76.0 g, 553 mmol) in DMF (100 mL) was added 2-chloroacetyl chloride (23.0 g, 15.3 mL, 203 mmol) drop-wise. The reaction mixture was heated at 80° C. overnight then cooled to ambient temperature and poured into water (300 mL). The precipitate was collected by filtration, washed with water and dried to give 6-bromo-7-fluoro-4H-benzo[1,4]oxazin-3-one (41.0 g, 90%). 1H NMR (DMSO-d6, 400 MHz): δ 7.13 (m, 2H), 4.62 (s, 2H). The amide proton was not observed.

후처리

  1. temperaturethen cooled to ambient temperature
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customdried

출처 및 근거

ORD 기록
ord-4e30714f7a4844399e079571929e9e4a
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09115151B2

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