N-bromobutanimide → 4-(4-Chlorobenzoyl)-3-chlorobenzyl bromide

HRID 280639노트

반응식

HRID 280639 반응식
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:9]=2[Cl:15])=[O:7])=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O>C1C=CC=CC=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][Br:18])=[CH:10][C:9]=2[Cl:15])=[O:7])=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 136496494-(4-Chlorobenzoyl)-3-chlorotoluene

생성물 1

HCID 136496544-(4-Chlorobenzoyl)-3-chlorobenzyl bromide수율 49.2%

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매2회HCID 241Benzene용매

실험 절차

A stirred refluxing solution of 4-(4-chlorobenzoyl)-3-chlorotoluene (2.65 g, 9.99 mmol) and dibenzoylperoxide (100 mg, 0.413 mmol) in benzene (100 ml) was treated in portions with an intimate mixture of N-bromosuccinimide (2.2 g, 12. mmol) and dibenzoylperoxide (100 mg, 0.413 mmol). The mixture was refluxed 1.5 hours, cooled, and filtered. The filtrate was evaporated under vacuum, triturated with diethyl ether (100 ml), and filtered. The filtrate was evaporated under vacuum and the residue was chromatographed on silica gel (500 g) eluted with 97:3 (v/v) n-hexane-ethyl acetate using a preparative highperformance liquid chromatograph to provide 1.69 g (49%) of 4-(4-chlorobenzoyl)-3-chlorobenzyl bromide, m.p. 88°-90° C.

후처리

  1. temperatureThe mixture was refluxed 1.5 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customThe filtrate was evaporated under vacuum
  5. customtriturated with diethyl ether (100 ml)
  6. filtrationfiltered
  7. customThe filtrate was evaporated under vacuum
  8. customthe residue was chromatographed on silica gel (500 g)
  9. washeluted with 97:3 (v/v) n-hexane-ethyl acetate using a preparative highperformance liquid chromatograph

출처 및 근거

ORD 기록
ord-f82d02ae12bd4e0cbd96e9329d9ca9e1
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04590201

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