Dimethyl Sulfoxide → 1255713-68-8

HRID 1253933Notes

Reaction equation

HRID 1253933 reaction equation
[Br:1][C:2]1[C:3]([F:12])=[CH:4][C:5]2[O:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=1.[CH3:13]S(C)=O.CI.C(=O)([O-])[O-].[K+].[K+]>O>[Br:1][C:2]1[C:3]([F:12])=[CH:4][C:5]2[O:9][C:8](=[O:10])[N:7]([CH3:13])[C:6]=2[CH:11]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 6679786932273-01-1

Product 1

HCID 667977351255713-68-8

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A flask was charged with 5-bromo-6-fluorobenzo[d]oxazol-2(3H)-one (3.6 g, 14.74 mmol) and DMSO (150 mL), and MeI (4.18 g, 29.5 mmol) and potassium carbonate (5.09 g, 36.9 mmol) were added. The mixture was stirred at room temperature overnight. The mixture was poured to water (1.2 L) and the precipitate was filtered, washed with water and dried under high vacuum at 60° C. for 1 h to give 5-bromo-6-fluoro-3-methylbenzo[d]oxazol-2(3H)-one. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.32 (s, 3H) 7.62 (d, J=8.34 Hz, 1H) 7.70 (d, J=6.06 Hz, 1H).

Workup

  1. additionwere added
  2. filtrationthe precipitate was filtered
  3. washwashed with water
  4. customdried under high vacuum at 60° C. for 1 h

Sources & evidence

ORD record
ord-b6ddd81ca7cd4c4386eac7164d8dd5f0
Source dataset
uspto-grants-2013_06
Patent number
US08455522B2

Reaction notes

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