Water → HCID 67003514, compound

HRID 2199697Notes

Reaction equation

HRID 2199697 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:11][CH3:12])(=[O:10])[CH2:8][SH:9].[Br:13][C:14]1[C:15](F)=[C:16]([CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1)[CH:17]=O.O>CC#N>[Br:13][C:14]1[C:15]2[S:9][C:8]([C:7]([O:11][CH3:12])=[O:10])=[CH:17][C:16]=2[CH:19]=[C:20]([C:22]([F:23])([F:24])[F:25])[CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 74891939HCID 74891939, compound

Product 1

HCID 67003514HCID 67003514, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potassium carbonate (1.44 g, 10.42 mmol) then methyl thioglycolate (0.487 g, 4.59 mmol) were added to a degassed solution of 3-bromo-2-fluoro-5-(trifluoromethyl)benzaldehyde (1.13 g, 4.17 mmol) in CH3CN (11 mL). The mixture was stirred at room temperature for 30 minutes then refluxed at 100° C. overnight. The mixture was allowed to cool to room temperature, then water (20 mL) was added. The resulting light yellow solid was collected by vacuum filtration, washed with water, then dried in vacuo. The resulting ester was used directly for the following step. 1H NMR (500 MHz, CDCl3) δ 8.24 (br s, 1H); 8.15 (br s, 1H); 7.86 (br s, 1H); 4.02 (br s, 3H). LC1: 4.00 min. Compound does not ionize.

Workup

  1. temperaturethen refluxed at 100° C. overnight
  2. temperatureto cool to room temperature
  3. filtrationThe resulting light yellow solid was collected by vacuum filtration
  4. washwashed with water
  5. customdried in vacuo
  6. custom4.00 min

Sources & evidence

ORD record
ord-d062e74ccb00436085fa6996c1cddd4d
Source dataset
uspto-grants-2016_06
Patent number
US09359339B2

Reaction notes

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