Sodium Hydroxide → HCID 89713970, compound

HRID 880222Notes

Reaction equation

HRID 880222 reaction equation
[CH3:1][C:2]([S@:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[Br:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1.[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[Br:8][C:9]1[CH:16]=[CH:15][C:12](/[CH:13]=[N:7]\[S@@:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 707414-BromobenzaldehydeHCID 10964479tert-Butylsulfinamide, (R)-(+)-

Product 1

HCID 89713970HCID 89713970, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Add (R)-2-methylpropane-2-sulfinamide (40.5 g, 0.33 mol) portion-wise to a solution of 4-bromobenzaldehyde (65.57 g, 0.35 mol) in toluene (283 mL). Stir the mixture at ambient temperature for 15 minutes and then add sodium hydroxide (1.34 g, 0.33 mol). Stir the suspension at ambient temperature for 12 h. Add sodium sulphate (16 g) and Celite® (16 g) and stir the suspension for 15 min. Filter and concentrate the filtrate under reduced pressure. Purify the residue by silica gel chromatography eluting with hexane/EtOAc (100% to 70% hexane) to afford the title compound as a white solid (85.5 g, 88% yield). MS (m/z): 288 (M+1).

Workup

  1. stirringStir the suspension at ambient temperature for 12 h
  2. filtrationFilter
  3. concentrationconcentrate the filtrate under reduced pressure
  4. customPurify the residue by silica gel chromatography
  5. washeluting with hexane/EtOAc (100% to 70% hexane)

Sources & evidence

ORD record
ord-d322f1c020b240c8933126d56a8f97d0
Source dataset
uspto-grants-2015_03
Patent number
US08993568B2

Reaction notes

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