Hydrogen Bromide → HCID 23442900, compound

HRID 2119675Notes

Reaction equation

HRID 2119675 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11](=[O:13])(=[O:12])[CH2:10][CH2:9][C:8]=2[CH:14]=1)(=[O:3])[CH3:2].[BrH:15].BrBr>C(O)(=O)C>[Br:15][CH2:2][C:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11](=[O:12])(=[O:13])[CH2:10][CH2:9][C:8]=2[CH:14]=1)=[O:3]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24408Bromine2×HCID 23442925HCID 23442925, compound

Product 1

HCID 23442900HCID 23442900, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5-acetyl-2,3-dihydrobenzothiophene-1,1-dioxide (8 g, 38.1 mmol) (obtained in preparation 17) dissolved in acetic acid (45 ml) under argon atmosphere, aqueous HBr (0.5 ml, 47%), bromine (5.84 g, 36.54 mmol) was added slowly at 15°-20° C. and the reaction mixture was stirred for about 0.5 h. Additional quantity of bromine (4.84 g) was slowly added and the stirring continued for further 10 h at 25°-30° C. Argon atmosphere was removed and the reaction mixture was kept open in the wave of blowing air in the fuming cup board to eliminate free bromine. The solid separated was filtered and washed with acetic acid (2×10 ml) followed by pet. ether to yield the title compound (10 g, 91%). mp. 68°-70° C.

Workup

  1. waitthe stirring continued for further 10 h at 25°-30° C
  2. customArgon atmosphere was removed
  3. customThe solid separated
  4. filtrationwas filtered
  5. washwashed with acetic acid (2×10 ml)

Sources & evidence

ORD record
ord-c9fc0591040943fcac14e8de9705896a
Source dataset
uspto-grants-2004_02
Patent number
US06686390B2

Reaction notes

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