2-Phenylacetophenone → 3-(3-Bromo-4-iodo-phenyl)-1,2-diphenyl-propan-1-one

HRID 724603Notes

Reaction equation

[C:1]1([C:7]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].[Br:22][C:23]1[CH:28]=[C:27]([CH2:29]Br)[CH:26]=[CH:25][C:24]=1[I:31]>O1CCCC1>[Br:22][C:23]1[CH:28]=[C:27]([CH2:29][CH:9]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:8])[CH:26]=[CH:25][C:24]=1[I:31]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of deoxybenzoin (26.4 mg, 0.134 mmol) in tetrahydrofuran (0.66 mL) was cooled to −78° C. and potassium tert-butoxide (0.15 mL, 0.15 mmol, 1.0 M in tetrahydrofuran) was added dropwise. The reaction mixture was stirred at −78° C. for 10 minutes and 2-bromo-4-(bromomethyl)-1-iodobenzene (50.0 mg, 0.133 mmol) in tetrahydrofuran (1 mL) was added dropwise. The reaction mixture was warmed to 25° C. and quenched with saturated ammonium chloride (5 mL) and extracted with ethyl acetate (2×5 mL). The combined organic extracts were washed with brine (5 mL), dried with magnesium sulfate, filtered, and concentrated to a crude yellow oil which was purified by flash column chromatography to yield the desired product (65 mg, 42%). LCMS found for C21H17BrIO (M+H)+: m/z=491, 493.

Workup

temperatureThe reaction mixture was warmed to 25° C.
customquenched with saturated ammonium chloride (5 mL)
extractionextracted with ethyl acetate (2×5 mL)
washThe combined organic extracts were washed with brine (5 mL)
dry with materialdried with magnesium sulfate
filtrationfiltered
concentrationconcentrated to a crude yellow oil which
customwas purified by flash column chromatography

Sources & evidence

ORD record: ord-b4913cee67a54743bdeec87029faad54
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141596B2

Reaction notes

Loading…