Bromine → HCID 67625499, compound

HRID 1418804Notes

Reaction equation

HRID 1418804 reaction equation
[CH3:1][C:2]1[C:7]2[C:8]3([CH2:13][CH2:14][S:15][C:6]=2[C:5]([CH3:16])=[CH:4][C:3]=1[C:17]([OH:19])=[O:18])[S:12][CH2:11][CH2:10][S:9]3.BrBr.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH3:16][C:5]1[C:6]2[S:15][CH2:14][C:13]3[S:9][CH2:10][CH2:11][S:12][C:8]=3[C:7]=2[C:2]([CH3:1])=[C:3]([C:17]([OH:19])=[O:18])[CH:4]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 10957942HCID 10957942, compound

Product 1

HCID 67625499HCID 67625499, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 0.62 g of 2,3-dihydro-5,8-dimethylspiro[4H-1-benzothiopyran-4,2'-[1,3]dithiolane]-6-carboxylic acid in 200 mL of chloroform was cooled to 0° C. To this mixture was added a solution of 0.38 g of bromine in 20 mL of chloroform dropwise. The resulting mixture was stirred overnight at room temperature. To this reaction mixture was added 10% aqueous sodium thiosulfate. 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 gave 0.29 g of the title compound of Step A as a purple solid melting at 250° C. (dec.). 1H NMR (CDCl3): δ 2.35 (s, 3H), 2.70 (s, 3H), 3.05 (m, 2H), 3.39 (br s, 2H), 3.41 (m, 2H), 7.66 (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-709f600f88164482bfac2ae4c0c4f1fa
Source dataset
uspto-grants-1999_03
Patent number
US05885936

Reaction notes

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