Water → 3-Hydroxy-5-nitrobenzotrifluoride

Temperature

-80 °C

3-Methoxy-5-nitrobenzotrifluoride (5 g, 23 mmol) was dissolved in anhydrous methylene chloride (100 mL) and cooled to -80° C. under a nitrogen atmosphere. To this solution was added via dropping funnel a 1M solution of BBr3 in methylene chloride (68 mL, 68 mmol). This solution was allowed to warm to room temperature and stirred for 3 days. Water was slowly added to the mixture and mixed well to quench the excess BBr3. To this mixture ether (500 mL) was added. The organic layer was separated and extracted with 2N NaOH (240 mL). The alkaline extract was neutralized with dilute HCl and extracted with diethyl ether (3×300 mL). The ether extracts were combined, washed with saturated NaCl and dried over anhydrous MgSO4. Evaporation of diethyl ether gave a brownish yellow oil which was chromatographed on a silica column to give 1.6 g (34%) of a yellow solid. 1H-NMR (CDCl3 /CD3OD; 300 MHz) δ 7.38-7.40 (m, 1H), 7.82 (t, 1H, J=2.2 Hz), and 7.95-7.96 (m, 1H).

1. additionTo this solution was added
2. temperatureto warm to room temperature
3. additionmixed well
4. customto quench the excess BBr3
5. additionTo this mixture ether (500 mL) was added
6. customThe organic layer was separated
7. extractionextracted with 2N NaOH (240 mL)
8. extractionThe alkaline extract
9. extractionextracted with diethyl ether (3×300 mL)
10. washwashed with saturated NaCl
11. dry with materialdried over anhydrous MgSO4
12. customEvaporation of diethyl ether
13. customgave a brownish yellow oil which
14. customwas chromatographed on a silica column

ORD record

ord-91e0b9bf68654c9c83310d4212628a2c

Source dataset

uspto-grants-2000_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06034127