Acetic Acid → 3-(Trifluoromethyl)-4-(benzyloxy)nitrobenzene

Sodium hydride (1.8 g, of a 60% dispersion in oil, 45 mmol) was added in portions to a stirred solution of benzyl alcohol (10.8 g, 100 mmol) in DMA (100 ml) with vigorous stirring under an atmosphere of nitrogen at ambient temperature. After warming to 45° C. for 30 minutes the mixture was cooled to ambient temperature and added dropwise to a stirred solution of 2-chloro-5-nitro-trifluoromethylbenzene (11.3 g, 50 mmol) in DMA (30 ml), keeping the temperature below 10° C. The mixture was stirred at 25° C. for 1 hour, then acidified with acetic acid and evaporated to give a yellow solid. The residue was dissolved in dichloromethane, washed with water then dried (MgSO4), and evaporated. The residue was suspended in a mixture of hexane (70 ml) and diethyl ether (10 ml) and the resulting solid filtered off to give 2-benzyloxy-5-nitro-trifluoromethylbenzene (6.6 g, 49%).

1. temperatureAfter warming to 45° C. for 30 minutes the mixture
2. temperaturewas cooled to ambient temperature
3. customthe temperature below 10° C
4. stirringThe mixture was stirred at 25° C. for 1 hour
5. customevaporated
6. customto give a yellow solid
7. washwashed with water
8. dry with materialthen dried (MgSO4)
9. customevaporated
10. additionThe residue was suspended in a mixture of hexane (70 ml) and diethyl ether (10 ml)
11. filtrationthe resulting solid filtered off

ORD record

ord-ddbb54bb420f4947a6d94ef5210a45a7

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08492560B2