Sodium Carbonate → 5-[2-(Trifluoromethoxy)phenyl]-2-thiophenecarboxaldehyde

HRID 1394153Notes

Reaction equation

HRID 1394153 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1Br.[CH:13]([C:15]1[S:19][C:18](B(O)O)=[CH:17][CH:16]=1)=[O:14].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OC(=O)C)C.CC([O-])=O.CC([O-])=O.[Pd+2].O>[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:18]1[S:19][C:15]([CH:13]=[O:14])=[CH:16][CH:17]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27734305-Formyl-2-thiopheneboronic acidHCID 27772661-Bromo-2-(trifluoromethoxy)benzene

Product 1

HCID 167686785-[2-(Trifluoromethoxy)phenyl]-2-thiophenecarboxaldehyde

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-trifluoromethoxy-1-bromobenzene (0.21 mL) and 5-formyl-2-thiophene boronic acid (0.23 g) in DME (11 mL) were added Pd(OAc)2 (0.014 g) and Ph3P (0.033 g) followed by 2M sodium carbonate (1 mL) and water (1 mL). The mixture was stirred at rt for 3 h. The reaction was diluted with ethylacetate (20 mL) and washed with water and brine, and then dried (sodium sulfate). The crude product was purified by flash-chromatography using acetone-hexanes (1:4) to give the desired 5-(2-trifluoromethoxyphenyl)thiophene-2-aldehyde as an oil [MS data: m/e 273 (M+1)+]. The aldehyde (0.15 g), thus obtained, was then condensed with 2,4-thiazolidine-2,4-dione in the presence of benzoic acid and piperidine under the conditions described in EXAMPLE 5 to give the title compound 5-(5-(2-trifluoromethoxyphenyl)thienylidene)thiazolidine-2,4-dione.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (sodium sulfate)
  3. customThe crude product was purified by flash-chromatography

Sources & evidence

ORD record
ord-83e75f9df52e4f699f967937269e0883
Source dataset
uspto-grants-2008_03
Patent number
US07348348B2

Reaction notes

Loading…