4-Fluorophenyl isocyanate → HCID 58158465, compound

HRID 2095827Notes

Reaction equation

HRID 2095827 reaction equation
Br.[Br:2][CH:3]([CH3:7])[CH2:4][CH2:5][NH2:6].[F:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]=[C:16]=[O:17])=[CH:11][CH:10]=1>N1C=CC=CC=1>[Br:2][CH:3]([CH3:7])[CH2:4][CH2:5][NH:6][C:16]([NH:15][C:12]1[CH:13]=[CH:14][C:9]([F:8])=[CH:10][CH:11]=1)=[O:17]

Participants

4

Reactant 2

HCID 709554-Fluorophenyl isocyanateHCID 87219297HCID 87219297, compound

Product 1

HCID 58158465HCID 58158465, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-bromobutane-1-aminehydrobromide (2270 mg, 9.7 mmol) in pyridine (18 mL) was slowly added 1-fluoro-4-isocyanatobenzene (1600 mg, 12 mmol) under ice-cooling, and the mixture was stirred at room temperature for 2 hr. The solvent was evaporated under reduced pressure, ethyl acetate/tetrahydrofuran and 0.5N aqueous hydrochloric acid solution were added to the residue, and the aqueous layer was extracted with ethyl acetate/tetrahydrofuran (×3). The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the residue was washed with ethyl acetate/hexane (=1/1) to give the title compound (1750 mg, 62%) as a white solid.

Workup

  1. temperaturecooling
  2. customThe solvent was evaporated under reduced pressure, ethyl acetate/tetrahydrofuran and 0.5N aqueous hydrochloric acid solution
  3. additionwere added to the residue
  4. extractionthe aqueous layer was extracted with ethyl acetate/tetrahydrofuran (×3)
  5. washThe combined organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. washthe residue was washed with ethyl acetate/hexane (=1/1)

Sources & evidence

ORD record
ord-c91da8ba9b2c4a59b357989ac6db6bb8
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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