2-Bromo-4-nitroanisole → 2-Bromo-4-nitrophenol

Temperature

115 °C

2-Bromo-4-nitroanisole (20 g, 0.086 mol) was dissolved in DMF (414 mL) at rt under N2. Sodium ethylthiolate (17.4 g, 0.207 mol) was added and the reaction mixture was warmed to 115° C. for 2 h. The reaction was cooled to rt and diluted with EtOAc (200 mL) and 1 M HCl (aq., 200 mL). The phases were separated, and the desired product was extracted into 1 M NaOH (aq, 150 mL×3). The basic aqueous extracts were combined and acidified using conc. HCl. The desired product was extracted from the acidic aqueous solution using EtOAc (250 mL×2). The combined organic layers were washed with brine and dried over sodium sulfate. The volatiles were removed in vacuo to afford a light brown semi-solid (9.8 g, 52% yield). 1H NMR (DMSO-d6) δ 8.33 (m, 1H); 8.09 (m, 1H); 7.07 (d, 1H).

1. temperatureThe reaction was cooled to rt
2. customThe phases were separated
3. extractionthe desired product was extracted into 1 M NaOH (aq, 150 mL×3)
4. extractionThe desired product was extracted from the acidic aqueous solution
5. washThe combined organic layers were washed with brine
6. dry with materialdried over sodium sulfate
7. customThe volatiles were removed in vacuo

ORD record

ord-386c8385adeb4aa98954a8240b9ccd39

Source dataset

uspto-grants-2005_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06933299B1