Water → HCID 10621601, compound

HRID 1031712Notes

Reaction equation

HRID 1031712 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[C:16]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:15][C:9]2[C:10](=[O:14])[CH2:11][CH2:12][O:13][C:8]=2[CH:7]=1)(=[O:4])=[O:3].[Br:24]Br.O>C(Cl)(Cl)Cl>[Br:24][CH:11]1[C:10](=[O:14])[C:9]2[CH:15]=[C:16]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])=[CH:7][C:8]=2[O:13][CH2:12]1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 10806538HCID 10806538, compound

Product 1

HCID 10621601HCID 10621601, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 300 ml of chloroform was dissolved 33.3 g of 2,3-dihydro-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one. To this solution being maintained at 25°-30° C. was dropwise added 16.3 g of bromine in 30 minutes. After the completion of the dropwise addition, the mixture was stirred for 30 minutes at 25°-30° C. 100 ml of water was added thereto. The organic layer was separated, washed with a 5% aqueous sodium thiosulfate solution, water and a saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to obtain 40.1 g (yield: 97.3%) of 3-bromo-2,3-dihydro-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one.

Workup

  1. temperatureTo this solution being maintained at 25°-30° C.
  2. customin 30 minutes
  3. additionAfter the completion of the dropwise addition
  4. customThe organic layer was separated
  5. washwashed with a 5% aqueous sodium thiosulfate solution, water
  6. dry with materiala saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-04e36da916864fcd850abd73732c0508
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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