Acetic Acid → 6-bromo-4-hydroxy-chromene-2-thione

HRID 1636429Notes

Reaction equation

HRID 1636429 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[OH:11])(=[O:3])[CH3:2].[C:12](=S)=[S:13].CC(C)([O-])C.[K+].C(O)(=O)C>C1(C)C=CC=CC=1>[Br:10][C:8]1[CH:7]=[CH:6][C:5]2[O:11][C:12]([SH:13])=[CH:2][C:1](=[O:3])[C:4]=2[CH:9]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6348Carbon DisulfideHCID 959915'-Bromo-2'-hydroxyacetophenoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 116589266-bromo-4-hydroxy-chromene-2-thione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 2-acetyl-4-bromophenol (20 g) and carbon disulfide (7 ml) in toluene (400 ml) was added dropwise to a suspension of potassium tert.-butoxide (31.4 g) in toluene (500 ml) at 10° C. The mixture was stirred at room temperature for 72 hours. Glacial acetic acid (35 ml) was added and the mixture evaporated under reduced pressure. The residue was treated with water (200 ml) and glacial acetic acid (20 ml) to precipitate an oily solid. Light petroleum (b.p. 40-60° C.) was added and the mixture stirred for one hour, filtered and the solid was collected and washed with light petroleum to give 6-bromo-2-mercapto-4H-1-benzopyran-4-one, m.p. 230° C. (compound 1)

Workup

  1. customthe mixture evaporated under reduced pressure
  2. additionThe residue was treated with water (200 ml) and glacial acetic acid (20 ml)
  3. customto precipitate an oily solid
  4. additionLight petroleum (b.p. 40-60° C.) was added
  5. stirringthe mixture stirred for one hour
  6. filtrationfiltered
  7. customthe solid was collected
  8. washwashed with light petroleum

Sources & evidence

ORD record
ord-56ef612ac3cd4eca9e7046a030eaedfe
Source dataset
uspto-grants-2000_03
Patent number
US06034121

Reaction notes

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