4-Bromo-2-fluorobenzaldehyde → HCID 86696069, compound

HRID 718497Notes

Reaction equation

CC(C)([O-])C.[K+].IP(C1C=CC=CC=1)(C1C=CC=CC=1)(C1C=CC=CC=1)[CH2:9][CH:10]1[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][CH3:18])[CH2:12][CH2:11]1.[Br:37][C:38]1[CH:45]=[CH:44][C:41]([CH:42]=O)=[C:40]([F:46])[CH:39]=1>C1COCC1>[Br:37][C:38]1[CH:45]=[CH:44][C:41]([CH:42]=[CH:9][CH:10]2[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][CH3:18])[CH2:12][CH2:11]2)=[C:40]([F:46])[CH:39]=1

Participants

Conditions

Temperature: -30 °C

Procedure

Under a nitrogen atmosphere, potassium t-butoxide (30.4 g, 271.0 mmol) was added, at −30° C. or lower, to a THF (500 mL) suspension of iodotriphenyl((4-propylcyclohexyl)methyl)phosphine (73) (143.0 g, 271.0 mmol). The reaction mixture was agitated at −30° C. or lower for 1 hour, and then a THF (100 mL) solution of 4-bromo-2-fluorobenzaldehyde (50.0 g, 246.0 mmol) was added dropwise thereto. The reaction mixture was returned to room temperature, and then quenched with 500 mL of water, and extracted with 200 mL of toluene three times. Combined organic layers were washed with water and saturated brine, and then dried over magnesium sulfate, and a solvent was distilled off by an evaporator. The residue was purified by silica gel column chromatography, and thus 4-bromo-2-fluoro-1-(2-(4-propylcyclohexyl)vinyl)benzene (75) (75.0 g, yield 94.0%) was obtained.

Workup

customwas returned to room temperature
customquenched with 500 mL of water
extractionextracted with 200 mL of toluene three times
washCombined organic layers were washed with water and saturated brine
dry with materialdried over magnesium sulfate
distillationa solvent was distilled off by an evaporator
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-80f80bc18cdb4d61aa05967680fd4f80
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193908B2

Reaction notes

Loading…