Sodium Hydroxide → HCID 89713970, compound

HRID 1518948Notes

Reaction equation

HRID 1518948 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) portionwise 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 hours. Add sodium sulphate (16 g) and Celite® (16 g), and stir the suspension for 15 minutes. Then filter and concentrate the filtrate under vacuum. Purify the residue by silica gel chromatography eluting with hexane/ethyl acetate (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 hours
  2. filtrationThen filter
  3. concentrationconcentrate the filtrate under vacuum
  4. customPurify the residue by silica gel chromatography
  5. washeluting with hexane/ethyl acetate (100% to 70% hexane)

Sources & evidence

ORD record
ord-98c3426759764d31957017f3bc624364
Source dataset
uspto-grants-2015_07
Patent number
US09073856B2

Reaction notes

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