Potassium Carbonate → HCID 68872701, compound

HRID 2112036Notes

Reaction equation

HRID 2112036 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=1.[C:15]([O:24][CH3:25])(=[O:23])[C:16]1[C:17](=[CH:19][CH:20]=[CH:21][CH:22]=1)[SH:18].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[C:11]([O:10][C:6]1[CH:5]=[C:4]([CH2:3][CH2:2][S:18][C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[C:15]([O:24][CH3:25])=[O:23])[CH:9]=[CH:8][CH:7]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 68872917HCID 68872917, compound

Product 1

HCID 68872701HCID 68872701, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(2-Bromoethyl)-3-tert-butoxybenzene (320 mg, 1.244 mmol) was dissolved in acetonitrile (15 ml). Methyl thiosalicylate (209 mg, 1.244 mmol) was added and then potassium carbonate, anhydrous (258 mg, 1.866 mmol) was added. The mixture was heated to reflux for 3 hours and then evaporated under vacuum to dryness. Chromatography of the residue on a column (ISOLUTE® SI, 5 g/25 ml) using ethyl acetate/heptane (5:95) as eluant gave 421 mg desired product, yield 98%.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. customevaporated under vacuum to dryness

Sources & evidence

ORD record
ord-f496b5a7aff04dac869fa2c8a8c1c207
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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