Water → HCID 21099420, compound

HRID 1351656Notes

Reaction equation

HRID 1351656 reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[Br:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([O-:19])=[O:18])=[CH:13][CH:12]=1.[Na+].CN(C)CCN.O>CS(C)=O>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])(=[O:19])=[O:18])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 66053N,N-DimethylethylenediamineHCID 811292-BromobenzaldehydeHCID 23670685Sodium 4-bromobenzene-1-sulfinate

Product 1

HCID 21099420HCID 21099420, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

2-Bromobenzaldehyde (1.55 g, 8.4 mmol), sodium 4-bromophenylsulfinate (2.79 g, 10 mmol) and copper(I) trifluoromethanesulfonate benzene complex (500 mg, 1 mmol) were combined in dimethylsulfoxide (10 mL) under nitrogen and degassed. The suspension was heated to 110° C. and N,N-dimethylethylenediamine (176 mg, 2 mmol) was added. The reaction was heated until the colour became clear and pale yellow, then cooled and poured into water. The products were extracted into ethyl acetate. The organic layer was washed with water: brine (1:1, ×5), dried over MgSO4 and evaporated in vacuo. The residue was triturated with isohexane to give 2-[(4-bromophenyl)sulfonyl]benzaldehyde (1.5 g, 55%). δH (400 z, CDCl3): 10.76 (1H, s), 8.14–8.12 (1H; m), 7.98–7.96 (1H, m), 7.76–7.68 (4H, m), 7.64–7.62 (2H, m).

Workup

  1. customdegassed
  2. temperatureThe reaction was heated until the colour
  3. temperaturepale yellow, then cooled
  4. extractionThe products were extracted into ethyl acetate
  5. washThe organic layer was washed with water: brine (1:1, ×5)
  6. dry with materialdried over MgSO4
  7. customevaporated in vacuo
  8. customThe residue was triturated with isohexane

Sources & evidence

ORD record
ord-b432582e458a4935b34a33efb32fc5d8
Source dataset
uspto-grants-2007_05
Patent number
US07217740B2

Reaction notes

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