m-Chloroperbenzoic acid → 1-Methylethyl 2-(4-methoxy-[1,1′-biphenyl]-3-yl)diazenecarboxylate 2-oxide
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][C:4]=1[N:15]=[N:16][C:17]([O:19][CH:20]([CH3:22])[CH3:21])=[O:18].ClC1C=CC=C(C(OO)=[O:31])C=1>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][C:4]=1[N+:15]([O-:31])=[N:16][C:17]([O:19][CH:20]([CH3:22])[CH3:21])=[O:18]Participants
Procedure
A solution of 1-methylethyl (4-methoxy-[1,1′-biphenyl]-3-yl)diazenecarboxylate (10.25 g) in dichloromethane (160 mL) was cooled in an ice bath and meta-chloroperbenzoic acid (14.8 g) was added in portions with stirring. Additional dichloromethane (90 mL) was added and the solution left to stir at room temperature for 3 days. To the mixture, dichloromethane (200 mL) was added and washed with saturated potassium bicarbonate (300 mL), followed by saturated sodium sulfite (2×200 mL) and finally saturated potassium bicarbonate (200 mL). The organic phase was dried with sodium sulfate and evaporated to give the product as a brown-orange solid (9.78 g). The product was purified using silica gel chromatography (1:5 ethyl acetate:hexane). Evaporation of the desired fractions gave purified product as an orange solid (6.19 g), with melting point 102-106° C. The product was analyzed by NMR (CDCl3) which showed 1.4 d (6H), 3.9 s (3H), 5.2 m (1H), 7.1-7.9 m (8H), where d signifies doublet, s signifies singlet, and m signifies multiplet; and by LC/MS which showed m/z: 315.8 (M+H)+, (M)+ 314.7.
Workup
- waitthe solution left
- stirringto stir at room temperature for 3 days
- washwashed with saturated potassium bicarbonate (300 mL)
- dry with materialThe organic phase was dried with sodium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-edbb2d1407944e10a6863d654c15a5cf
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07511029B2
Reaction notes
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