Tetrahydrofuran → HCID 66616500, compound

Participants

Reaction Conditions

Reaction Steps

To a 500 mL 3-neck round bottom flask fitted with condenser and nitrogen tube, was added N1,N2-bis(4-fluorobenzyl)phthalamide (2 g, 5.2 mmol, 1 eq) and THF (HPLC grade 100 mL). The clear solution was cooled to 0° C., before borondimethylsulphide (12 g, 15 mL, 164 mmol, 30 eq) was added slowly. The reaction mixture refluxed for 36 h, cooled to −10° C. to −15° C. and treated with methanol slowly through a dropping funnel until frothing stopped (50 mL). The reaction mixture concentrated to dryness and once again cooled to 0° C., before methanol (100 mL) was added slowly, The reaction mixture was refluxed for 40 h and concentrated under vacuum to dryness to give the crude product (1.5 g, 85%) as a solid, which was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ 7.32-7.28 (m 6H), 7.22-7.19 (m, 2H), 7.10-7.05 (m, 4H), 3.72-3.64 (m, 8H). MS (ESI): 353.2 (M+H)+.

Provenance & Evidence