1,2-Dichloroethane → HCID 87231630, compound

Participants

Reaction Steps

Add (S)-(−)-2-methyl-2-propanesulfinamide (15 g, 73.89 mmol) to a stirring mixture of 2-bromo-4-fluorobenzaldehyde (9.85 g, 81.28 mmol) in 1,2-dichloroethane (50 mL) at RT. And then add Ti(OEt)4 (25.28 g, 4.78 mol) to the mixture and stir overnight at RT. Cool the reaction in an ice/water bath, and dilute with water. Filter the reaction mixture over a ½ inch pad of celite, and wash the filtered stuff with dichloromethane (4×150 mL). Separate the organic layer and wash the aqueous layer with 150 mL DCM. Combine the organic layers, dry over MgSO4, filter, and concentrate. Purify the residue via silica chromatography eluting with hexanes to 8:2 hexanes:ethyl acetate. Pool the desired fractions and concentrate to give the product as a very pale yellow oil (21.5 g, 95%). GCMS m/z 305 [M]+.

Provenance & Evidence