Potassium Carbonate → HCID 21099498, compound

HRID 2376957Notes

Reaction equation

HRID 2376957 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[SH:17].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 805982-Bromobenzenethiol

Product 1

HCID 21099498HCID 21099498, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

4-fluorobenzaldehyde (10 mL, 93 mmol), 2-bromobenzenethiol (12 mL, 102 mmol) and potassium carbonate (15.4 g, 111 mmol) were combined in dimethylsulfoxide (50 mL) under nitrogen and heated to 120° C. After 2 hours, the temperature had reached 210° C. so the reaction was stopped. The cooled reaction mixture was partitioned between water and ethyl acetate. The organic layer was dried over Na2SO4 and the solvent removed in vacuo. The residue was purified by flash column chromatography on silica, eluting with 10% ethyl acetate/isohexane, to give 4-[(2-bromophenyl)thio]benzaldehyde (23.83 g, 87%). δH (360 MHz, d6 DMSO): 9.97 (1H, s), 7.89-7.82 (3H, m), 7.55-7.33 (5H, m).

Workup

  1. customhad reached 210° C.
  2. customThe cooled reaction mixture
  3. customwas partitioned between water and ethyl acetate
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customthe solvent removed in vacuo
  6. customThe residue was purified by flash column chromatography on silica
  7. washeluting with 10% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-219790f025064f668cac927137a873ef
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Reaction notes

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