Bromine → HCID 67574013, compound

HRID 1418811Notes

Reaction equation

HRID 1418811 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[C:9]([CH3:15])=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]12[S:19][CH2:18][CH2:17][S:16]1.BrBr.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[C:9]([CH3:15])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]1[S:19][CH2:18][CH2:17][S:16][C:7]=12

Participants

5

Reactant 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 88292580HCID 88292580, compound

Product 1

HCID 67574013HCID 67574013, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a mixture of 1.2 g of the title compound of Step C in 150 mL of chloroform was added a solution of 0.76 g of bromine in 30 mL of chloroform dropwise. The mixture was stirred overnight at room temperature. To this reaction mixture was then added 10% aqueous sodium thiosulfate. The organic layer was separated, dried over MgSO4, filtered, and concentrated under reduced pressure to dryness. The resulting solid was crystallized from 1-chlorobutane to gave 0.65 g of the title compound of Step D as a yellow solid melting at 205° C. (dec.). 1H NMR ((CD3)2SO): δ 2.58 (s, 3H), 2.91 (s, 3H), 2.98 (m, 2H), 3.49 (m, 2H), 7.47 (d, 1H), 7.49 (s, 1H), 7.73 (d, 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 solid was crystallized from 1-chlorobutane

Sources & evidence

ORD record
ord-c150623ea6ca4cf8b2f112d7e7ab25e4
Source dataset
uspto-grants-1999_03
Patent number
US05885936

Reaction notes

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