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

HRID 280639ノート

反応式

HRID 280639 の反応式
[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

参加物

5

反応物 2

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

生成物 1

HCID 136496544-(4-Chlorobenzoyl)-3-chlorobenzyl bromide収率 49.2%

試薬・触媒・溶媒 2

HCID 7187Benzoyl Peroxide触媒2 回HCID 241Benzene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f82d02ae12bd4e0cbd96e9329d9ca9e1
出典データセット
uspto-grants-1986_05
特許番号
US04590201

反応ノート

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