Trimethyl phosphite → HCID 90403884, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]([C:11]=1[F:12])=[N+:7]([O-])[O:8][N:9]=2.P(OC)(OC)OC>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2=[N:9][O:8][N:7]=[C:6]2[C:11]=1[F:12]Participants
3
Conditions
- Temperature
- 95 °C
Procedure
6-Bromo-7-fluorobenzo[c][1,2,5]oxadiazole 1-oxide (1.2 g, 5.0 mmol) was added to neat trimethyl phosphite (6.2 g, 50 mmol) and heated to 95° C. for 2 h. After cooling the solution was deposited on silica gel and chromatographed with a 0-10% ethyl acetate-hexane gradient to give the partially purified product which was further purified by Kugelrohr distillation to give the title compound as low melting, white crystals (460 mg, 43%): 1H NMR (400 MHz, CDCl3) δ 7.61 (m, 1H), 7.51 (dd, J=9.4, 5.6 Hz, 1H); 19F NMR (376 MHz, CDCl3) δ −111.68; EIMS m/z 216.
Workup
- temperatureAfter cooling the solution
- customchromatographed with a 0-10% ethyl acetate-hexane gradient
- customto give the partially purified product which
- distillationwas further purified by Kugelrohr distillation
Sources & evidence
- ORD record
- ord-d5f4e89631dd493e99a1d52082c3f4bc
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09006250B2
Reaction notes
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