Iodine → Methyl 3-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzoate

HRID 82239Notes

Reaction equation

HRID 82239 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1([C:6]2[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=2)[C:9]([O:11][CH2:12]C)=[O:10])[NH:5][NH:4]1.C(N(CC)CC)C.II>CO>[F:18][C:2]([F:1])([F:17])[C:3]1([C:6]2[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=2)[C:9]([O:11][CH3:12])=[O:10])[N:4]=[N:5]1

Participants

5

Reactant 3

HCID 807IodineHCID 8471TriethylamineHCID 70817635HCID 70817635, compound

Product 1

HCID 11096832Methyl 3-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzoateYield 27%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Ethyl 3-(3-(trifluoromethyl)diaziridin-3-yl)benzoate (Preparation 199, 226 mg, 0.87 mmol) was stirred in methanol (10 mL) with triethylamine (0.36 mL, 2.61 mmol). Iodine (662 mg, 2.61 mmol) was dissolved in 2 mL methanol and added portion-wise until an orange-brown colour persisted. The reaction mixture was evaporated in vacuo and the residue was diluted with 1M aq. NaOH (30 mL) and then extracted with EtOAc (3×30 mL). The combined organic extracts were dried (MgSO4) and evaporated in vacuo to afford the title compound as a gum in 27% yield, 60 mg. This material was used in the next step without further purification.

Workup

  1. additionadded portion-wise until an orange-brown colour
  2. customThe reaction mixture was evaporated in vacuo
  3. additionthe residue was diluted with 1M aq. NaOH (30 mL)
  4. extractionextracted with EtOAc (3×30 mL)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-6c340ca70cd844e28a49253f17522851
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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