反应详情

To a solution of 3-bromo-4-methylbenzoic acid (5.0 g, 0.023 mol) in CH2CH2 (100 mL) was added oxalyl chloride (8.67 g, 0.069 mol). After 10 minutes, 1.0 mL of DMF was added slowly and the mixture was continued to stir at RT for 2 hours. The volatile was removed in vacuo. The residue was re-dissolved in CH2CH2 (100 mL) and transferred to a 125 mL additional funnel. To a 500 mL Erlenmeyer flask equipped with a stir bar was added 100 m]L of sat. aq. NaHCO3 solution followed by 2.79 g of (R)-α-methylbenzylamine (0.023 mol) in 100 mL of CH2CH2. 3-Bromo-4-methylbenzoyl chloride in CH2Cl2 (from above) was added dropwise to the Erlenmeyer flask and the reaction mixture was continued to stir at RT for 16 hours. The organic phase was diluted with 50 mL of CH2CH2, separated from aqueous phase, dried over Na2SO4 and concentrated in vacuo. The residue was washed with 50 mL of Et2O and dried in an oven at 40 C overnight to afford light yellow solid (7.0 g, 0.022 mol, 96%).

1. customThe volatile was removed in vacuo
2. dissolutionThe residue was re-dissolved in CH2CH2 (100 mL)
3. customtransferred to a 125 mL additional funnel
4. customTo a 500 mL Erlenmeyer flask equipped with a stir bar
5. additionwas added 100 m]L of sat. aq. NaHCO3 solution
6. stirringto stir at RT for 16 hours
7. additionThe organic phase was diluted with 50 mL of CH2CH2
8. customseparated from aqueous phase
9. dry with materialdried over Na2SO4
10. concentrationconcentrated in vacuo
11. washThe residue was washed with 50 mL of Et2O
12. customdried in an oven at 40 C overnight