Potassium Carbonate → HCID 799201, compound

HRID 2234148Notes

Reaction equation

HRID 2234148 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]([C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)=[O:10].[Br:16][C:17]1[CH:24]=[C:21]([CH:22]=O)[C:20]([OH:25])=[CH:19][CH:18]=1>CC(C)=O>[Br:16][C:17]1[CH:18]=[CH:19][C:20]2[O:25][C:8]([C:9]([C:11]3[S:12][CH:13]=[CH:14][CH:15]=3)=[O:10])=[CH:22][C:21]=2[CH:24]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 728635-BromosalicylaldehydeHCID 27763722-Bromo-1-(thiophen-2-yl)ethan-1-one

Product 1

HCID 799201HCID 799201, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (12.0 g, 0.087 mol) and subsequently 2-bromo-1-(thiophen-2-yl)ethanone (7.0 g, 0.034 mol; prepared as described in J. Med. Chem. 30, 1497 (1987)) were added to a stirred solution of 5-bromosalicylaldehyde (6.9 g, 0.034 mol) in acetone (150 mL). The mixture was stirred at ambient temperature for 30 min at first and then refluxed for 1 h. Solid mass was filtered off, washed with hot acetone (2×50 mL) and the filtrate was evaporated in vacuo. The residue (11.3 g) was crystallized from ethanol (15 mL) giving (5-bromobenzo[b]furan-2-yl)-(thiophen-2-yl)methanone. Yield: 8.0 g (77%). M.p. 84-86° C. RF (SiO2, hexane/ethyl acetate 3:1) 0.70.

Workup

  1. temperaturethen refluxed for 1 h
  2. filtrationSolid mass was filtered off
  3. washwashed with hot acetone (2×50 mL)
  4. customthe filtrate was evaporated in vacuo
  5. customThe residue (11.3 g) was crystallized from ethanol (15 mL)

Sources & evidence

ORD record
ord-2af53ace97104a9eb98bc3f50331af93
Source dataset
uspto-grants-2010_05
Patent number
US07709528B2

Reaction notes

Loading…