Dichloromethane → HCID 86083501, compound

HRID 2367142Notes

Reaction equation

HRID 2367142 reaction equation
[C:1]([C:3]1[C:4]([F:17])=[C:5]([NH:9]C(=O)OC(C)(C)C)[CH:6]=[CH:7][CH:8]=1)#[CH:2].FC(F)(F)C(O)=O.[Cl:25]CCl>C(O)(C)C.Cl.O1CCOCC1>[ClH:25].[C:1]([C:3]1[C:4]([F:17])=[C:5]([CH:6]=[CH:7][CH:8]=1)[NH2:9])#[CH:2]

Participants

7

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 86083509Carbamic acid, (3-ethynyl-2-fluorophenyl)-, 1,1-dimethylethyl ester

Product 1

HCID 86083501HCID 86083501, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 3776IsopropanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1,1-dimethylethyl (3-ethynyl-2-fluorophenyl)carbamate (10.5 g, 44.6 mmol) in dichloromethane (100 mL) was added trifluoroacetic acid (20 mL). The solution was stirred at room temperature for 1 hr, and was then concentrated in-vacuo. The resultant residue was partition between sodium bicarbonate and ether. The organic portion was washed with brine, dried over sodium sulfate, filtered and concentrated in-vacuo to afford a brown residue. The residue was diluted with isopropanol (10 mL) and 4N HCl in dioxane (8 mL) was added. The recrystallized product was collected by vacuum filtration to afford 3.7 g, 21 mmol (68%) of 3-ethynyl-2-fluoroaniline hydrochloride as a pale brown solid. 1H NMR (400 MHz, d6-DMSO): 7.08-6.91 (m, 3H), 4.45 (s, 1H); MS (EI) for C8H6FN: 136 (MH+).

Workup

  1. concentrationwas then concentrated in-vacuo
  2. customThe resultant residue was partition between sodium bicarbonate and ether
  3. washThe organic portion was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in-vacuo
  7. customto afford a brown residue
  8. additionwas added
  9. filtrationThe recrystallized product was collected by vacuum filtration

Sources & evidence

ORD record
ord-a76d7d6bd890465fb75dddf2e25180a4
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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