Dimethylformamide → 2-(4-Bromophenoxy)acetamide

To a solution of (4-bromophenoxy)acetic acid (500 mg, 2.00 mmol) in dichloromethane (10 mL) and DMF (0.2 mL) was added 2M oxalyl chloride in methylene chloride (5 mL, 10 mmol). The reaction mixture was stirred at room temperature for 2 hours, and the solvent was removed under reduced pressure. Ammonium hydroxide (15 mL) was added dropwise via additional funnel. After addition, the mixture was extracted with EtOAc (3×20 mL). The combined organic layers were dried and concentrated in vacuo to give 2-(4-bromophenoxy)acetamide (350 mg, 70% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 7.37-7.35 (m, 2H), 6.81-6.79 (m, 2H), 4.59 (s, 2H).

1. customthe solvent was removed under reduced pressure
2. additionAmmonium hydroxide (15 mL) was added dropwise via additional funnel
3. additionAfter addition
4. extractionthe mixture was extracted with EtOAc (3×20 mL)
5. customThe combined organic layers were dried
6. concentrationconcentrated in vacuo

ORD record

ord-0d40f7466eff4c9ca72219133632cc17

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08889730B2