4-Bromobenzaldehyde → (R)-N-(4-bromobenzylidene)-2-methylpropane-2-sulfinamide

HRID 1525252Notes

Reaction equation

HRID 1525252 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][C:11]([S@:14]([NH2:16])=[O:15])([CH3:13])[CH3:12].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>ClCCl.[O-]S([O-])(=O)=O.[Cu+2]>[Br:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[N:16]/[S@@:14]([C:11]([CH3:13])([CH3:12])[CH3:10])=[O:15])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 707414-BromobenzaldehydeHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 10964479tert-Butylsulfinamide, (R)-(+)-

Product 1

HCID 12195522(R)-N-(4-bromobenzylidene)-2-methylpropane-2-sulfinamideYield 69%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
37 °C

Procedure

To a mixture of 4-bromobenzaldehyde, 18-a, (150 g, 0.82 mol) in dichloromethane (1.5 L) were added (R)-2-methylpropane-2-sulfinamide (128 g, 1.06 mol), PPTS (20 g, 0.08 mmol) and anhydrous CuSO4 (394 g, 2.46 mol) and the resulting mixture was stirred at 37° C. overnight. The mixture was then filtrated and the filtrate was concentrated under vacuum. The residue was purified by column chromatography (petroleum ether/ethyl acetate=5/1) to provide the product, 18-b, (200 g, 69%).

Workup

  1. filtrationThe mixture was then filtrated
  2. concentrationthe filtrate was concentrated under vacuum
  3. customThe residue was purified by column chromatography (petroleum ether/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-551ba661de304f919e3e53f6a0df0e2c
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

Loading…