1,2-Dichlorobenzene → Benzene, 1,2-bis(phenylmethyl)-

HRID 485957

反応式

HRID 485957 の反応式
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1Cl.CC[Mg+].[Br-].[C:13]1([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.ClC1C=CC=CC=1CC1C=CC=CC=1>CCOCC.C1COCC1>[CH2:14]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:13][C:19]=1[CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 72391,2-Dichlorobenzene2 回HCID 7647DibenzylHCID 123431Benzene, 1-chloro-2-(phenylmethyl)-HCID 178461630HCID 178461630、化合物

生成物 1

HCID 10934161Benzene, 1,2-bis(phenylmethyl)-収率 38.4%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒3 回HCID 8028Tetrahydrofuran溶媒

実験手順

This Example illustrates the use of EtMgBr/[NitriphosCl]PF6 as an activator/catalyst to improve yield. To 2.00 g (13.61 mmoles) of o-dichlorobenzene, 0.050 g (0.065 mmoles) of [NitriphosCl]PF6 in 5 mL of ether at 0° C. was added 0.5 mL (1.5 mmoles) of 2.9M EtMgBr in ether. After stirring for 0.5 hrs, 30 mL of ether and 7.0 mL (14 mmoles) of 2M benzylMgCl in THF were added. The mixture was refluxed for 3 days and worked up as usual. After removing the solvent, the residue was distilled at 0.1 mm to initially remove 0.550 g (3.7 mmoles, 27%) of o-dichlorobenzene and then 1.482 g (bp: 68° to 83° C.) of a clear liquid was collected. 1H NMR spectrum in CDCl3 indicated a 10:1 ratio of 1-chloro-2-benzylbenzene to bibenzyl (representing 6.7 mmoles (67 % based on reacted o-dichlorobenzene) of 1-chloro-2-benzylbenzene and 0.67 mmoles of bibenzyl). The material that remained in the pot was chromatographed on silica gel eluted with 10% EtOAc/hexane to give 0.602 g (2.57 mmoles, 19%) of 1,2-dibenzylbenzene (mp: 61° to 67° C.).

後処理

  1. customto improve yield
  2. temperatureThe mixture was refluxed for 3 days
  3. customAfter removing the solvent
  4. custom1.482 g (bp: 68° to 83° C.) of a clear liquid was collected
  5. custompot was chromatographed on silica gel
  6. washeluted with 10% EtOAc/hexane

出典と根拠

ORDレコード
ord-3aa0f4bbd4fe4f7aa0b802077bdc6964
出典データセット
uspto-grants-1985_08
特許番号
US04538003

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