Benzoyl Peroxide → 2-(3-Bromomethylbenzo[d]isoxazol-6-yloxy)-5-fluorobenzonitrile

HRID 1715599노트

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HRID 1715599 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][C:11]2[CH:20]=[CH:19][C:14]3[C:15]([CH3:18])=[N:16][O:17][C:13]=3[CH:12]=2)=[C:6]([CH:9]=1)[C:7]#[N:8].[Br:21]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>ClC1C=CC=CC=1Cl>[Br:21][CH2:18][C:15]1[C:14]2[CH:19]=[CH:20][C:11]([O:10][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:9][C:6]=3[C:7]#[N:8])=[CH:12][C:13]=2[O:17][N:16]=1

참가 물질

5

반응물 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 574841185-Fluoro-2-(3-methyl-benzo[d]isoxazol-6-yloxy)-benzonitrile

생성물 1

HCID 674092672-(3-Bromomethylbenzo[d]isoxazol-6-yloxy)-5-fluorobenzonitrile수율 26.1%

시약·촉매·용매 1

HCID 72391,2-Dichlorobenzene용매

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온도
150 °C

실험 절차

5-fluoro-2-(3-methyl-benzo[d]isoxazol-6-yloxy)-benzonitrile (3v), (0.87 g, 3.2 mmol), N-bromosuccinimide (0.82 g, 4.6 mmol), benzoyl peroxide (0.12 g, 0.49 mmol) and o-dichlorobenzene (6 mL) were combined in a 15 mL pressure tube. The mixture was stirred and heated in a 150° C. bath. After 2.5 hours the reaction was cooled and the residue was purified directly by column chromatography (silica, 70% CH2Cl2/hexanes) to provide compound (4v) (0.29 g, 26% yield) plus recovered starting material (3v) (0.57 g, 65%). 1H NMR (400 MHz, CDCl3) δ 7.84 (d, J=7.0 Hz, 1H), 7.45-7.43 (m, 1H), 7.35-7.31 (m, 1H), 7.16-7.13 (m, 2H), 7.08-7.05 (m, 1H), 4.72 (s, 2H).

후처리

  1. temperatureAfter 2.5 hours the reaction was cooled
  2. customthe residue was purified directly by column chromatography (silica, 70% CH2Cl2/hexanes)

출처 및 근거

ORD 기록
ord-46d187e930e04c789afdf200cab2597a
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07799782B2

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