Acetonitrile → 1-(Allyloxy)-2-bromo-5-chloro-4-(4-ethoxybenzyl)benzene

HRID 1410293Notes

Reaction equation

[Br:1][C:2]1[C:3]([O:20][CH3:21])=[CH:4][C:5]([Cl:19])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH3:18])=[CH:12][CH:11]=2)=O)[CH:7]=1.[C:22](#N)[CH3:23].C([SiH](CC)CC)C.B(F)(F)F.CCOCC>ClCCl>[CH2:21]([O:20][C:3]1[CH:4]=[C:5]([Cl:19])[C:6]([CH2:8][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH3:18])=[CH:12][CH:11]=2)=[CH:7][C:2]=1[Br:1])[CH:22]=[CH2:23]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred −10° C. solution of (5-Bromo-2-chloro-4-methoxyphenyl)(4-ethoxyphenyl)methanone (54.3 mmol) from Step 4 in dichloromethane (150 mL)/acetonitrile (150 mL) was added triethylsilane (20 mL, 109 mmol) followed by boron trifluoride diethyl etherate (16 mL, 109 mmol) at −10° C. The solution was allowed to warm to 0° C. over 2 h prior to quenching with saturated sodium carbonate solution. After removal of organic volatiles under reduced pressure, the residue was partitioned between ethyl acetate and water. Following extraction of the aqueous layer with ethyl acetate, the combined organic layers were washed with water prior to drying over magnesium sulfate. Filtration and concentration under reduced pressure yielded the title compound as a yellowish solid which was used without further purification.

Workup

customto quenching with saturated sodium carbonate solution
customAfter removal of organic volatiles under reduced pressure
customthe residue was partitioned between ethyl acetate and water
extractionextraction of the aqueous layer with ethyl acetate
washthe combined organic layers were washed with water
dry with materialto drying over magnesium sulfate
filtrationFiltration and concentration under reduced pressure

Sources & evidence

ORD record: ord-4b6402c0fda64e8c95ec0c46eac0204f
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921412B2

Reaction notes

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