Hydrochloric Acid → HCID 86726414, compound

HRID 629800Notes

Reaction equation

HRID 629800 reaction equation
Cl.[F:2][C:3]1[C:4]([I:18])=[C:5]([NH:10]C(=O)OC(C)(C)C)[C:6]([F:9])=[CH:7][CH:8]=1>O1CCOCC1.C1COCC1>[F:2][C:3]1[C:4]([I:18])=[C:5]([C:6]([F:9])=[CH:7][CH:8]=1)[NH2:10]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86726415HCID 86726415, compound

Product 1

HCID 86726414HCID 86726414, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

4M HCl (7.60 mL, 30.4 mmol) in dioxane was added to a solution of tert-butyl (3,6-difluoro-2-iodophenyl)carbamate (1.08 g, 3.04 mmol) in THF (7.60 ml) at room temperature and then stirred overnight. The solvent was removed in vacuo, and then the contents were partitioned between DCM (3×50 mL) and sat'd aqueous sodium bicarbonate. The organics were dried over MgSO4, filtered and concentrated. The crude material was purified on silica gel, eluting 0-50% EtOAc in hexanes over 16 minutes to afford 3,6-difluoro-2-iodoaniline (373 mg, 1.46 mmol) as a tan oil. MS (ESI): m/z=256.2 (M+H-Boc).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe contents were partitioned between DCM (3×50 mL)
  3. dry with materialThe organics were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified on silica gel
  7. washeluting 0-50% EtOAc in hexanes over 16 minutes

Sources & evidence

ORD record
ord-efcbf90f21a6444f94f347465a246b0b
Source dataset
uspto-grants-2016_04
Patent number
US09315475B2

Reaction notes

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