Potassium Carbonate → 6-Methoxy-2-(4-bromo-4,4-difluorobutylthio)benzoxazole

HRID 2399727Notes

Reaction equation

HRID 2399727 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8]([SH:10])[O:9][C:5]=2[CH:4]=1.CS(O[CH2:18][CH2:19][CH2:20][C:21]([Br:24])([F:23])[F:22])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8]([S:10][CH2:18][CH2:19][CH2:20][C:21]([Br:24])([F:23])[F:22])[O:9][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 218503894-Bromo-4,4-difluorobutyl methanesulfonateHCID 178488033HCID 178488033, compound

Product 1

HCID 193843246-Methoxy-2-(4-bromo-4,4-difluorobutylthio)benzoxazole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 6-methoxy-2-mercaptobenzoxazole (1.77 g, 9.8 mmoles), 4-bromo-4,4-difluorobutyl methanesulphonate (2.4 g, 9 mmoles), potassium carbonate (5 g, 36.2 mmoles) and acetone (60 cm3) was stirred at the ambient temperature for 18 hours. The precipitate which formed was removed by filtration and the filtrate evaporated under reduced pressure to give a brown oil which was purified by chromatography on silica gel, eluted with a 1:4 mixture of ethyl acetate and hexane, to give the title intermediate product as a light yellow oil. 1H NMR (CDCl3): δ7.48(d,1H); 7.00(d,1H); 6.90(dd,1H); 3.85(s,3H); 3.38(t,2H); 2.50-2.68(m,2H).

Workup

  1. customThe precipitate which formed
  2. customwas removed by filtration
  3. customthe filtrate evaporated under reduced pressure
  4. customto give a brown oil which
  5. customwas purified by chromatography on silica gel
  6. washeluted with a 1:4 mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-243c57e3e5a74cdca7907117adc16060
Source dataset
uspto-grants-1995_09
Patent number
US05451594

Reaction notes

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