4-(bromomethyl)-N,N-diethylbenzamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,4-Dioxa-8-azaspiro[4.5]-decane (200 mmol, 28.6 g, 25.6 mL) is dissolved in 160 ml of dry acetonitrile under nitrogen and treated with K2CO3 (220 mmol, 30.3 g) followed by dropwise addition over 1.5 hours of 4-(bromomethyl)-N,N-diethylbenzamide (200 mmol, 54.01 g) as a solution in 81 mL of acetonitrile. After 16 hours, the reaction mixture is poured into 250 mL of water and extracted twice with 150 mL of methylene chloride. The pooled extracts were washed with 250 mL of brine, dried over Na2SO4 and concentrated in vacuo affording 63.9 g (192 mmol, 96% yield) of the product as a yellow-orange oil. extracted twice with 150 mL of methylene chloride The pooled extracts were washed with 250 mL of brine dried over Na2SO4 concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Bromomethylbenzoic acid (50 g, 233 mmol) is dissolved in 500 mL of tetrahydrofuran containing a few drops if N,N-dimethylformamide at room temperature under nitrogen and treated dropwise over 1 hour with oxalyl chloride (268 mmol, 34.0 g, 23.4 mL). After the addition, the reaction mixture is stirred for 0.5 hour, at which point the solvent is removed in vacuo. The solid residue is dissolved in 200 mL of tetrahydrofuran and poured into a rapidly stirring solution of diethylamine (536 mmol, 39.2 g, 55.7 mL) in 400 mL of water. After the mixture cools to room temperature, 100 mL of ether are added and the two phases are separated. The organic phase is dried over magnesium sulfate and concentrated in vacuo affording 54.01 g (200 mmol, 86% yield) of the product as a white solid. After the addition is removed in vacuo The solid residue is dissolved in 200 mL of tetrahydrofuran cools to room temperature the two phases are separated The organic phase is dried over magnesium sulfate concentrated in vacuo