Dichloromethane → HCID 18786749, compound

Participants

Reaction Steps

A solution of 3-iodo-5-nitrobenzyl fluoride (9.2 g, 32.7 mmol) described in Step C, in methanol (311 mL) was treated with TiCl3 (311 mL, >10 wt. % in 20-30 wt % HCl) and stirred at room temperature for 20 minutes. The reaction was poured into a separatory funnel containing 95:5 CH2Cl2 :MeOH and the aqueous layer was made basic with 15% aq. NaOH. The layers were separated and the aqueous layer was extracted with 95:5 CH2Cl2 :MeOH. The organic layers were combined, dried (MgSO4), filtered and concentrated to give an orange semi-solid. Purification by flash chromatography (3:1 to 1:1 hexane:methylene chloride) provided 3-amino-5-iodobenzyl fluoride as a tan solid: mp 48.5-50° C.

Provenance & Evidence