1-Mercapto-2-propanone → 1-(7-bromo-4H-thieno[3,2-c]chromen-2-yl)ethanone

HRID 1521794Notes

Reaction equation

HRID 1521794 reaction equation
C[O-].[Na+].[SH:4][CH2:5][C:6](=[O:8])[CH3:7].[Br:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14](Cl)=[C:15]([CH:20]=O)[CH2:16][O:17]2)=[CH:12][CH:11]=1>CO>[Br:9][C:10]1[CH:11]=[CH:12][C:13]2[C:14]3[S:4][C:5]([C:6](=[O:8])[CH3:7])=[CH:20][C:15]=3[CH2:16][O:17][C:18]=2[CH:19]=1

Participants

5

Reactant 3

HCID 5201441-Mercapto-2-propanoneHCID 10942334Sodium MethoxideHCID 897389707-bromo-4-chloro-2H-chromene-3-carbaldehyde

Product 1

HCID 897389921-(7-bromo-4H-thieno[3,2-c]chromen-2-yl)ethanone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of sodium methoxide (5.57 g, 103 mmol) in 250 ml of methanol at 0° C., mercaptoacetone (5.11 g, 57 mmol) was added portion-wise, and after 15 min., 7-bromo-4-chloro-2H-chromene-3-carbaldehyde (1a) (14 g, 52 mmol) was added to it portion-wise with stirring. After the addition, the ice bath was removed and the product gradually started precipitating out as a yellow solid. Stirring was continued for another 3 h, after which water was added to quench the reaction and the methanol was removed under vacuum. Addition of more water yielded the title compound as a yellow solid (1b) which was filtered and dried (14.1 g, 78%). m/z 308.9 (79Br) & 310.9 (81Br).

Workup

  1. additionAfter the addition
  2. customthe ice bath was removed
  3. customthe product gradually started precipitating out as a yellow solid
  4. stirringStirring
  5. waitwas continued for another 3 h
  6. additionafter which water was added
  7. customto quench
  8. customthe reaction
  9. customthe methanol was removed under vacuum
  10. additionAddition of more water

Sources & evidence

ORD record
ord-5622a86c3cf744fca03f8d99e4f9f999
Source dataset
uspto-grants-2015_07
Patent number
US09073942B2

Reaction notes

Loading…