Ethyl Acetate → HCID 18979100, compound

HRID 1423098Notes

Reaction equation

HRID 1423098 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([C:13]([F:16])([F:15])[F:14])[CH:9]=[CH:8]2.[Br:17]Br.[O-]S([O-])(=S)=O.[Na+].[Na+].CCOC(C)=O>CO>[Br:17][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:12]2[C:7]=1[CH:8]=[CH:9][C:10]([C:13]([F:16])([F:14])[F:15])=[N:11]2

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24408BromineHCID 24477Sodium ThiosulfateHCID 614880HCID 614880, compound

Product 1

HCID 18979100HCID 18979100, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The intermediate 8-methoxy-2-(trifluoromethyl)quinoline (2.21 g, 9.7 mmol) in MeOH (15 mL) was treated with a 1.5 N solution of bromine in MeOH (7.8 mL, 11.7 mmol) over a 15 min period. This mixture was stirred 2 h then treated with a 1 N aqueous solution of Na2S2O3 (30 mL) and EtOAc (300 mL). The phases where separated and the organic portion washed with brine, a saturated aqueous solution of NaHCO3, and again with brine. The organic phase was dried with Na2SO4, filtered, and evaporated to afford titled compound as a light brown solid. 1H NMR (CDCl3) 8.70 (dd, J=8.8, 0.6, 1H), 7.86 (d, J=8.8, 1H), 7.85 (d, J=8.4, 1H), 7.02 (d, J=8.4, 1H), 4.10 (s, 3H). LC/MS (Method B) 3.82 min, [M+1]+ 305/307.

Workup

  1. customThe phases where separated
  2. washthe organic portion washed with brine
  3. dry with materialThe organic phase was dried with Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-dc4869379f8a43f4a1e93a289a973b0a
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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