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

HRID 485957

반응식

HRID 485957 반응식
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

참가 물질

7

반응물 4

HCID 72391,2-Dichlorobenzene2회HCID 7647DibenzylHCID 123431Benzene, 1-chloro-2-(phenylmethyl)-HCID 178461630HCID 178461630, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매3회HCID 8028Tetrahydrofuran용매

실험 절차

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.).

후처리

  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

출처 및 근거

ORD 기록
ord-3aa0f4bbd4fe4f7aa0b802077bdc6964
출처 데이터셋
uspto-grants-1985_08
특허 번호
US04538003

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