Iodine → N-((3-fluoro-4-(trifluoromethoxy)phenyl)(oxazol-5-yl)methyl)-2-methylpropane-2-sulfinamide

HRID 2279447Notes

Reaction equation

HRID 2279447 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[C:4]([F:13])[CH:3]=1.II.[CH3:16][C:17]([S:20](/[N:22]=[CH:23]/[C:24]1[O:28][CH:27]=[N:26][CH:25]=1)=[O:21])([CH3:19])[CH3:18]>C1COCC1.C1(C)C=CC=CC=1>[F:13][C:4]1[CH:3]=[C:2]([CH:23]([C:24]2[O:28][CH:27]=[N:26][CH:25]=2)[NH:22][S:20]([C:17]([CH3:19])([CH3:18])[CH3:16])=[O:21])[CH:7]=[CH:6][C:5]=1[O:8][C:9]([F:12])([F:11])[F:10]

Participants

6

Reactant 3

HCID 807IodineHCID 27822174-Bromo-2-fluoro-1-(trifluoromethoxy)benzeneHCID 88924920HCID 88924920, compound

Product 1

HCID 86705473N-((3-fluoro-4-(trifluoromethoxy)phenyl)(oxazol-5-yl)methyl)-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 4-bromo-2-fluoro-1-(trifluoromethoxy)benzene (582 g, 2247 mmol), Mg (54.6 g, 2247 mmol) and iodine in THF (10 mL) was heated at reflux for 2 h. The reaction was cooled to 0° C. and added to a solution of (E)-2-methyl-N-(oxazol-5-ylmethylene)propane-2-sulfinamide (300 g, 1498 mmol, step 1 of example 1) in toluene (10 mL) cooled to 0° C. The reaction was stirred at 0° C. for 30 min. The reaction was quenched with water and extracted with DCM. The organic layer was concentrated to afford crude N-((3-fluoro-4-(trifluoromethoxy)phenyl)(oxazol-5-yl)methyl)-2-methylpropane-2-sulfinamide (55) which was used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. temperaturecooled to 0° C
  4. customThe reaction was quenched with water
  5. extractionextracted with DCM
  6. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-fb2f6f72ba314dacaefb342a25daac25
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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