4-Toluenesulfonyl chloride → HCID 21914298, compound

HRID 1669409Notes

Reaction equation

HRID 1669409 reaction equation
C([O-])([O-])=O.[K+].[K+].[Br:7][C:8]1[CH:14]=[CH:13][C:11]([OH:12])=[CH:10][C:9]=1[OH:15].[S:16](Cl)([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17]>CC(C)=O>[CH3:23][C:22]1[CH:24]=[CH:25][C:19]([S:16]([O:12][C:11]2[CH:13]=[CH:14][C:8]([Br:7])=[C:9]([OH:15])[CH:10]=2)(=[O:18])=[O:17])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 811054-Bromoresorcinol

Product 1

HCID 21914298HCID 21914298, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

K2CO3 (3 eq) was added to a stirred mixture of 4-bromoresorcinol (0.35 M) and TsCl (1.2 eq) in acetone and the mixture stirred at 50° C. for 18 h. Volatiles were removed in vacuo and the residue partitioned between 6 N HCl (aq) and EtOAc. The combined organic fractions were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo to give the title compound. The product was used in the next step without further purification. (ES+) m/z 343, 345 (M+H)+.

Workup

  1. customVolatiles were removed in vacuo
  2. customthe residue partitioned between 6 N HCl (aq) and EtOAc
  3. washThe combined organic fractions were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-19e5546efa4b4df8b8e80a99d1ab08d5
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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