Bromine → 2-Bromo-1-(3,4-dihydro-2H-1-benzothiopyran-6-yl)-1-propanone

HRID 980499Notes

Reaction equation

HRID 980499 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[S:11][CH2:10][CH2:9][CH2:8]2)(=[O:4])[CH2:2][CH3:3].C([O-])(O)=O.[Na+].[Br:20]Br>CCOCC>[Br:20][CH:2]([CH3:3])[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[S:11][CH2:10][CH2:9][CH2:8]2)=[O:4]

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 13257396HCID 13257396, compound

Product 1

HCID 137851022-Bromo-1-(3,4-dihydro-2H-1-benzothiopyran-6-yl)-1-propanoneYield 86%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 32 gr. of 6-propionyl-thiochromane in 400 ml of anhydrous ether, 8 ml of bromine are dropwise added, temperature being maintained at ±5° C. After addition, the mixture is still stirred for 2 to 3 hours at room temperature, than an aqueous saturated NaHCO3 solution is slowly added. The aqueous phase is twice extracted with 100 ml ether, combined organic phases are dried on MgSO4, filtered, and solvent is evaporated in vacuo. The residue so obtained is treated with 100 ml of petroleum ether; 38 gr. of α-bromo-6-propionyl-thiochromane are obtained.

Workup

  1. additionAfter addition
  2. additionis slowly added
  3. extractionThe aqueous phase is twice extracted with 100 ml ether
  4. customare dried on MgSO4
  5. filtrationfiltered
  6. customsolvent is evaporated in vacuo
  7. customThe residue so obtained

Sources & evidence

ORD record
ord-b2a06b10694345b68e4cbf0a415269b2
Source dataset
uspto-grants-1987_01
Patent number
US04638070

Reaction notes

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