4-Bromo-2-fluorobenzaldehyde → (NE,R)-N-[(4-bromo-2-fluorophenyl)methylidene]-2-methylpropane-2-sulfinamide

HRID 57418

Reaction equation

HRID 57418 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([F:10])[CH:3]=1.[CH3:11][C:12]([S@:15]([NH2:17])=[O:16])([CH3:14])[CH3:13]>S([O-])([O-])(=O)=O.[Cu+2].ClCCCl>[Br:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[N:17]/[S@@:15]([C:12]([CH3:14])([CH3:13])[CH3:11])=[O:16])=[C:4]([F:10])[CH:3]=1

Participants

5

Reactant 2

HCID 1435174-Bromo-2-fluorobenzaldehydeHCID 10964479tert-Butylsulfinamide, (R)-(+)-

Product 1

HCID 89479311(NE,R)-N-[(4-bromo-2-fluorophenyl)methylidene]-2-methylpropane-2-sulfinamideYield 103%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
55 °C

Procedure

To an oven dried round bottom flask with stir bar was added 4-bromo-2-fluorobenzaldehyde (5 g, 24.6 mmol), (R)-2-methylpropane-2-sulfinamide (3.28 g, 27.1 mmol) and DCE (49 mL). To this mixture was then added copper (II) sulfate (5.90 g, 36.9 mmol). Reaction mixture was heated in a preheated oil bath to 55° C. for 18 hours. Reaction mixture was filtered through a pad celite, washing the solids with CH2Cl2. The filtrate was concentrated to afford a viscous yellow oil of (R,E)-N-(4-bromo-2-fluorobenzylidene)-2-methylpropane-2-sulfinamide (7.73 g, 25.2 mmol, 103% yield). 1H NMR (400 MHz, CDCl3) δ 1.27 (s, 9H) 7.31-7.42 (m, 2H) 7.87 (t, J=7.87 Hz, 1H) 8.83 (s, 1H). LCMS m/z 307.9 (M+H)+, Rt 1.01 min.

Workup

  1. customTo an oven dried round bottom flask
  2. customReaction mixture
  3. customReaction mixture
  4. filtrationwas filtered through a pad celite
  5. washwashing the solids with CH2Cl2
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-089093fbdf924433a7243eb31dd67a6d
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Linked notes

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