N-bromobutanimide → 2-Amino-5-bromo-4-fluoro-benzoic acid

Temperature

-10 °C

To a solution of 2-amino-4-fluorobenzoic acid (10 g, 64.5 mmol) in N,N-dimethylformamide (100 mL) at −10° C., was added dropwise a solution of N-bromosuccinimide (11.2 g, 62.9 mmol) in N,N-dimethylformamide (50 mL) over 1 hour. After the addition was complete, the mixture was stirred at −10° C. for 1 hour. The reaction was quenched with aqueous sodium bisulfate and partitioned between ethyl acetate and water. The organic layer was separated, and the aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with water and then with brine, and then dried over sodium sulfate. The sample was concentrated to give the crude product 27 (14.5 g, yield: 96.5%), which was used for the next step without further purification.

1. additionAfter the addition
2. customThe reaction was quenched with aqueous sodium bisulfate
3. custompartitioned between ethyl acetate and water
4. customThe organic layer was separated
5. extractionthe aqueous layer was extracted twice with ethyl acetate
6. washThe combined organic layers were washed with water
7. dry with materialwith brine, and then dried over sodium sulfate
8. concentrationThe sample was concentrated

ORD record

ord-3f7a91a2acb742e59a13e66b35a835aa

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09061060B2