Dimethyl Sulfoxide → HCID 20065971, compound

HRID 359043Notes

Reaction equation

HRID 359043 reaction equation
[Br:1]N1C(=O)CCC1=O.C(O)(C)C.[C:13](=[O:15])=O.[CH3:16][C:17]1([CH3:37])[CH:26]=C[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([S:27]([C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[CH:23]=2)[O:18]1.CS(C)=O>O>[O:18]1[CH2:17][CH:16]=[C:13]([OH:15])[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]1=2.[Br:1][CH:26]1[C:17]([CH3:37])([CH3:16])[O:18][C:19]2[CH:24]=[CH:23][C:22]([S:27]([C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=3)(=[O:29])=[O:28])=[CH:21][C:20]=2[CH:13]1[OH:15]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 67184N-bromobutanimideHCID 14210534HCID 14210534, compoundHCID 86586944Isopropanol carbon dioxide

Product 1

HCID 20065971HCID 20065971, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

14.2 g (0.08 mol) of freshly recrystallized N-bromosuccinimide are introduced with cooling (isopropanol/dry ice) at about 15° C. into 12.6 g (0.04 mol) of 2,2-dimethyl-6-(4'-methylphenylsulfonyl)-chromene in a solution of 70 ml of dimethyl sulfoxide and 1.4 ml of water. The temperature rises temporarily to 27° C. The mixture is cooled to 20° C. and, after stirring for 1 hour, introduced into ice/ethyl acetate. The ethyl acetate phase is washed several times with water and dried over Na2SO4. On concentrating, the bromohydrin derivative crystallizes. Crystals of melting point: 141-142° C.

Workup

  1. customrises temporarily to 27° C
  2. washThe ethyl acetate phase is washed several times with water
  3. dry with materialdried over Na2SO4
  4. concentrationOn concentrating

Sources & evidence

ORD record
ord-254f3b9a914a47b5868de60c9f82645b
Source dataset
uspto-grants-1991_03
Patent number
US04999371

Reaction notes

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