2-Fluoro-5-(trifluoromethyl)phenyl isocyanate → HCID 59232016, compound

HRID 1091485Notes

Reaction equation

HRID 1091485 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)[CH:6]=[C:5]([F:18])[C:3]=1[NH2:4].[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:21]=1[N:30]=[C:31]=[O:32]>C1COCC1>[F:18][C:5]1[CH:6]=[C:7]([B:9]2[O:13][C:12]([CH3:14])([CH3:15])[C:11]([CH3:17])([CH3:16])[O:10]2)[CH:8]=[C:2]([F:1])[C:3]=1[NH:4][C:31]([NH:30][C:21]1[CH:22]=[C:23]([C:26]([F:27])([F:29])[F:28])[CH:24]=[CH:25][C:20]=1[F:19])=[O:32]

Participants

4

Reactant 2

HCID 27333802-Fluoro-5-(trifluoromethyl)phenyl isocyanateHCID 59231931HCID 59231931, compound

Product 1

HCID 59232016HCID 59232016, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,6-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.300 g, 1.18 mmol) in THF (2 mL) was added 1-fluoro-2-isocyanato-4-(trifluoromethyl)benzene (0.314 g, 1.53 mmol). The reaction was stirred at 45 C overnight. Solid product was present in the reaction vessel. Product was further precipitated by the addition of 1:3 ether/hexanes. The solids were collected by filtration, dried under hi vacuum and found to be clean title compound in 71% yield. 1H-NMR (DMSO-d6) δ 7.03 (dd, J=6.6, 1.8 Hz, 2H), 5.76 (s, 2H), 1.26 (s, 12H); MS [M+H]+=461.2, LCMS RT=4.11 min

Workup

  1. customProduct was further precipitated by the addition of 1:3 ether/hexanes
  2. filtrationThe solids were collected by filtration
  3. customdried under hi vacuum

Sources & evidence

ORD record
ord-20192ec8226c40798bf54ba0ee28ec14
Source dataset
uspto-grants-2012_03
Patent number
US08129379B2

Reaction notes

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