Tributylphosphine → 2-[2-(4-Bromophenyl)ethoxy]-1,3-dichloro-5-methylbenzene

HRID 561843

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[Cl:11][C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([Cl:19])[C:13]=1O.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC>CCOCC.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][C:13]2[C:12]([Cl:11])=[CH:17][C:16]([CH3:18])=[CH:15][C:14]=2[Cl:19])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

2-(4-Bromophenyl)ethanol (1 eq.) and 2,6-dichloro-4-methylphenol (1.5 eq.) were taken up in freshly deoxygenated toluene (0.1 M). To this solution was then added 1,1′-(azodicarbonyl)-dipiperidine (1.2 eq.) and finally tributylphosphine (1.2 eq.). The resulting yellow solution was heated at 80° C. for 2 h. The reaction mixture was cooled to RT, diluted with ether, and washed with 1 N aq. NaOH. The aqueous wash was back extracted with ether and the combined organic extracts were dried over MgSO4. Filtration and concentration of the filtrate in vacuo afforded a yellow semi-solid. Purification of the crude product thus obtained by way of flash chromatography (SiO2, Hex→10:1 (v/v) Hex:EtOAc) afforded the title compound as a colorless oil.

Workup

temperatureThe reaction mixture was cooled to RT
washwashed with 1 N aq. NaOH
washThe aqueous wash
extractionwas back extracted with ether
dry with materialthe combined organic extracts were dried over MgSO4
filtrationFiltration and concentration of the filtrate in vacuo
customafforded a yellow semi-solid
customPurification of the crude product
customthus obtained by way of flash chromatography (SiO2, Hex→10:1 (v/v) Hex:EtOAc)

Sources & evidence

ORD record: ord-8f57794e0e284dbb9b873e52c33bd924
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063105B2

Linked notes

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