N-bromobutanimide → 1-Bromo-5-methyl-3,3-bis(trifluoromethyl)-1,3-dihydro-1lambda3,2-benziodoxole

HRID 926923Notes

Reaction equation

HRID 926923 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=1[I:16])([OH:8])[C:4]([F:7])([F:6])[F:5].[Br:19]N1C(=O)CCC1=O>CC(O)C>[Br:19][I:16]1[C:10]2[CH:11]=[CH:12][C:13]([CH3:15])=[CH:14][C:9]=2[C:3]([C:4]([F:7])([F:6])[F:5])([C:2]([F:1])([F:17])[F:18])[O:8]1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 3295551,1,1,3,3,3-hexafluoro-2-(2-iodo-5-methylphenyl)propan-2-ol

Product 1

HCID 3269331-Bromo-5-methyl-3,3-bis(trifluoromethyl)-1,3-dihydro-1lambda3,2-benziodoxoleYield 100%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

Compound 2 (100 mg, 0.26 mmol) was dissolved in 5 mL propan-2-ol and N-bromosuccinimide (48.7 mg, 0.273 mmol) is added. The reaction mixture was heated 30 min at 50° C. After removal of the solvent under vacuum, the residue was purified over silica gel column using dichloromethane as eluant to give 111 mg (0.26 mmol, 92% yield) of a yellow solid.

Workup

  1. customAfter removal of the solvent under vacuum
  2. customthe residue was purified over silica gel column

Sources & evidence

ORD record
ord-335ffb6bbc2e4a95ae944d9ab678d386
Source dataset
uspto-grants-2016_03
Patent number
US09290421B2

Reaction notes

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