Nitric Acid → 2-Nitro-5-(trifluoromethoxy)benzyl bromide
Reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]([F:17])([F:16])[O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11][Br:12]>>[Br:12][CH2:11][C:10]1[CH:9]=[C:8]([O:7][C:6]([F:5])([F:16])[F:17])[CH:15]=[CH:14][C:13]=1[N+:1]([O-:4])=[O:2]Participants
3
Procedure
Fuming nitric acid (5 mL) was cooled to 0° C. and 3-(trifluoromethoxy)benzyl bromide (1 mL, 6.16 mmol) was added. After 15 minutes, the reaction was poured into ice water (100 mL) and extracted with EtOAc (200 mL). The organic layer was washed with water, saturated NaHCO3, and brine (75 mL each). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by flash chromatograpy on silica gel (0 to 15% EtOAc/hexanes) afforded 2-(bromomethyl)-1-nitro-4-(trifluoromethoxy)benzene Rf=0.54 (15% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) δ 8.14 (d, J=8.9 Hz, 1H), 7.43 (m, 1H), 7.31 (m, 1H), 4.82 (s, 2H).
Workup
- extractionextracted with EtOAc (200 mL)
- washThe organic layer was washed with water, saturated NaHCO3, and brine (75 mL each)
- dry with materialThe organic layer was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customPurification of the residue by flash chromatograpy on silica gel (0 to 15% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-b0c616c607aa4ad280c9a02a374bd925
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07652049B2
Reaction notes
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