Triethyl phosphite → 5-Bromo-6-chlorobenzo[c][1,2,5]oxadiazole

HRID 407113Notes

Reaction equation

HRID 407113 reaction equation
P(OCC)(OCC)OCC.[Br:11][C:12]1[C:13]([Cl:22])=[CH:14][C:15]2[C:16]([CH:21]=1)=[N+:17]([O-])[O:18][N:19]=2.[O-]Cl.[Na+]>C(O)C>[Br:11][C:12]1[C:13]([Cl:22])=[CH:14][C:15]2=[N:19][O:18][N:17]=[C:16]2[CH:21]=1

Participants

5

Reactant 3

HCID 31215Triethyl phosphiteHCID 23665760Sodium HypochloriteHCID 674650696-Bromo-5-chlorobenzo[c][1,2,5]oxadiazole 1-oxide

Product 1

HCID 674684685-Bromo-6-chlorobenzo[c][1,2,5]oxadiazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
79 °C

Procedure

P(OEt)3 (0.9 mL, 903 mg, 5.4 mmol) was added to a solution of bromide 93 (904 mg, 3.6 mmol) in ethanol at 79° C. The resulting mixture was stirred at 79° C. for 4 h. The mixture was then cooled in an ice bath and NaOCl (19 mL of a 10-15% sol, 1.2 g, 16 mmol) was added. The solution was cooled and concentrated under reduced pressure to provided crude 94.

Workup

  1. temperatureThe mixture was then cooled in an ice bath
  2. temperatureThe solution was cooled
  3. concentrationconcentrated under reduced pressure
  4. customto provided crude 94

Sources & evidence

ORD record
ord-451657bf30944838b09046134405184c
Source dataset
uspto-grants-2014_06
Patent number
US08754219B2

Reaction notes

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