3-Fluorobenzylamine → 3-Fluorobenzyl isocyanate

HRID 1685081Notes

Reaction equation

HRID 1685081 reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[F:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17][NH2:18].CCN(C(C)C)C(C)C>C(Cl)Cl>[F:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17][N:18]=[C:5]=[O:11]

Participants

5

Reactant 3

HCID 668533-FluorobenzylamineHCID 81531DiisopropylethylamineHCID 94429Triphosgene

Product 1

HCID 6434993-Fluorobenzyl isocyanateYield 110.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of triphosgene (2.37 g, 8 mmol) in CH2Cl2 (48 mL) was added dropwise a mixture of 3-fluorobenzylamine (2.0 g, 16 mmol) and DIPEA (4.14 g, 32 mmol) in CH2Cl2 (32 mL) over 2 hours at 0 C under N2 atmosphere. After addition was complete, the mixture was refluxed for 1 hour and then cooled to ambient temperature. The mixture was washed with aq. KHSO4, brine, dried over Na2SO4, and concentrated to give 3-fluorobenzyl isocyanate as a yellow liquid (1.34 g, yield 100%), which was used in the next step without further purification.

Workup

  1. additionAfter addition
  2. temperaturethe mixture was refluxed for 1 hour
  3. washThe mixture was washed with aq. KHSO4, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9f0978541960425e8f595c6cca606069
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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