Allyl bromide → 1-(Allyloxymethyl)-2-bromo-5-chloro-4-(4-ethylbenzyl)benzene

HRID 1175296Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][CH:10]=2)[C:5]([Cl:17])=[CH:4][C:3]=1[CH2:18][OH:19].[H-].[Na+].[CH2:22](Br)[CH:23]=[CH2:24]>CN(C=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[I-]>[CH2:24]([O:19][CH2:18][C:3]1[CH:4]=[C:5]([Cl:17])[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][CH:10]=2)=[CH:7][C:2]=1[Br:1])[CH:23]=[CH2:22]

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of (2-bromo-5-chloro-4-(4-ethylbenzyl)phenyl)methanol (3.4 g, 10 mmol) in DMF (50 mL) was added NaH (0.8 g, 20 mmol, 60% in miner oil) in portions at −5° C. After being stirred for 1 h at the same temperature, the reaction mixture was cooled to −10° C., TBAI (0.37 g, 1 mmol) and a solution of allyl bromide (1.45 g, 12 mmol) in DMF (10 mL) was added. The reaction mixture was stirred for another 1 h prior to quenching by ice water and extracted 3× with EtOAc. The combined organic layers were washed with brine and then dried over Na2SO4. Concentration gave the crude product, which was purified by silica column chromatography (elution with PE:EtOAc=10:1) to afford the title compound (3.22 g, yield 84.8%).

Workup

stirringThe reaction mixture was stirred for another 1 h
customto quenching by ice water
extractionextracted 3× with EtOAc
washThe combined organic layers were washed with brine
dry with materialdried over Na2SO4
concentrationConcentration
customgave the crude product, which
customwas purified by silica column chromatography (elution with PE:EtOAc=10:1)

Sources & evidence

ORD record: ord-8b01a15909f149b8970b8d65b2ab05a1
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07838498B2

Reaction notes

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