Sodium borohydride → HCID 67572167, compound
Reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[C:6]([N+:9]([O-])=O)[CH:5]=[CH:4][C:3]=1[S:12][CH3:13].[BH4-].[Na+]>CO.CCOCC.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:1][C:2]1[C:7]([CH3:8])=[C:6]([NH2:9])[CH:5]=[CH:4][C:3]=1[S:12][CH3:13]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of 2-bromo-4-nitro-methylthioanisole (450 mg, 1.81 mmol) in 45 mL of MeOH was added a suspension of copper(11) acetate (85 mg, 0.47 mmol) in 9 mL of MeOH. Sodium borohydride (300 mg, 7.9 mmol) was added as a solid over 0.5 h. The reaction was diluted with Et2O, washed with NaHCO3, dried with Na2SO4, filtered, and conc. to give 387 mg of the title compound. MS:m/e=218 (M+1) 1H NMR (400 Mhz, CDCl3): δ 2.35 (s, 3H), 6.62 (dd, 1H), 6.94 (d, 1H), 7.08 (d, 1H)
Workup
- washwashed with NaHCO3
- dry with materialdried with Na2SO4
- filtrationfiltered
Sources & evidence
- ORD record
- ord-732119a0e9e04a1f8458c7a5d8ad476b
- Source dataset
- uspto-grants-1999_03
- Patent number
- US05877191
Reaction notes
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