Bromine → HCID 67624138, compound

HRID 1418807Notes

Reaction equation

HRID 1418807 reaction equation
[CH3:1][C:2]1[C:7]2[C:8]3([CH2:13][CH2:14][S:15](=[O:17])(=[O:16])[C:6]=2[C:5]([CH3:18])=[CH:4][C:3]=1[C:19]([OH:21])=[O:20])[S:12][CH2:11][CH2:10][S:9]3.BrBr.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH3:18][C:5]1[C:6]2[S:15](=[O:16])(=[O:17])[CH2:14][C:13]3[S:12][CH2:11][CH2:10][S:9][C:8]=3[C:7]=2[C:2]([CH3:1])=[C:3]([C:19]([OH:21])=[O:20])[CH:4]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 86753937HCID 86753937, compound

Product 1

HCID 67624138HCID 67624138, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 0.50 g of the title compound of Step A in 200 mL of chloroform was cooled to 0° C. To this mixture was added a solution of 0.45 g of bromine in 35 mL of chloroform dropwise. The mixture was stirred at room temperature for 2 h and then 10% aqueous sodium thiosulfate solution was added. The organic layer was separated and dried over MgSO4, filtered, and concentrated under reduced pressure to dryness. The resulting residue was crystallized from 1-chlorobutane to yield 0.41 g of the title compound of Step B as a solid melting at 145° C. (dec.). 1H NMR (CDCl3): δ 2.49 (s, 3H), 2.56 (s, 3H), 3.11 (br s, 2H), 3.48 (m, 2H), 4.24 (br s, 2H), 7.57 (s, 1H).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure to dryness
  5. customThe resulting residue was crystallized from 1-chlorobutane

Sources & evidence

ORD record
ord-a409fcba3ea043dfb4e8a37fb8af85eb
Source dataset
uspto-grants-1999_03
Patent number
US05885936

Reaction notes

Loading…