Acetic Acid → HCID 13929409, compound

HRID 1607317Notes

Reaction equation

HRID 1607317 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([F:11])([F:10])[F:9].[Mg].[N:13]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[N:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].C(O)(=O)C>C1COCC1>[C:25]([O:24][C:22]([N:13]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([F:11])([F:10])[F:9])[NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:23])([CH3:28])([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 9806Benzene, 1-bromo-2-(trifluoromethyl)-HCID 97268Di-tert-butyl azodicarboxylateHCID 5462224Magnesium2×

Product 1

HCID 13929409HCID 13929409, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-75 °C

Procedure

2-Bromobenzotrifluoride (4.5 g, 20 mmol) and magnesium turnings (0.54 g, 22 mmol) were refluxed under a nitrogen atmosphere in 100 ml THF until the magnesium had dissolved. The resulting solution was cooled to -75° C. and added to 4.6 g (20 mmol) di-t-butyl azodicarboxylate in 100 ml THF at -75° C. The solution was warmed to -40° C., acetic acid (1.5 ml, 25 mmol) was added, and the mixture concentrated to 20 ml. Hexane and water were added, and the hexane solution was evaporated to leave a brown oil which was chromatographed on silica with 10% ether in CHCl3, providing 6.1 g (81% yield) of N,N'-bis(t-butoxycarbonyl)-2-(trifluoromethyl)phenylhydrazine as a brown gum. This material was dissolved in 200 ml isopropanol, and hydrogen chloride gas was passed into the solution resulting in a weight gain of 8 g. The solution was stirred at 50° C. for 30 minutes, then evaporated to dryness. The residue was treated with ether, and the solids collected by filtration and dried in vacuo, providing 2.7 g (79% yield) 2-(trifluoromethyl)phenylhydrazine hydrochloride as a white powder, mp 241°-242° C.

Workup

  1. dissolutionhad dissolved
  2. temperatureThe solution was warmed to -40° C.
  3. concentrationthe mixture concentrated to 20 ml
  4. additionHexane and water were added
  5. customthe hexane solution was evaporated
  6. customto leave a brown oil which
  7. customwas chromatographed on silica with 10% ether in CHCl3

Sources & evidence

ORD record
ord-05d877c0c48a4b0cbc8fca1fcae8e407
Source dataset
uspto-grants-1989_09
Patent number
US04864032

Reaction notes

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