3-Bromobenzaldehyde → HCID 89462449, compound

HRID 1525286Notes

Reaction equation

HRID 1525286 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[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:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)/[CH:5]=[N:16]/[S@:14]([C:11]([CH3:13])([CH3:12])[CH3:10])=[O:15]

Participants

6

Reactant 3

HCID 765833-BromobenzaldehydeHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 89462449HCID 89462449, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
37 °C

Procedure

3-bromobenzaldehyde, 24-a, (30 g, 162 mmol) in dichloromethane (600 ml) were added (S)-2-methylpropane-2-sulfinamide (23.52 g, 194.5 mmol), PPTS (5.97 g, 16.2 mmol) and anhydrous CuSO4 (78 g, 486 mmol) 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, 25-a, (24.5 g, 52%).

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-9b4311da15b54bca82d590c9d5616fee
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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