2-Fluoro-5-(trifluoromethyl)phenyl isocyanate → HCID 58696172, compound

HRID 1094850Notes

Reaction equation

HRID 1094850 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]=[CH:5][C:3]=1[NH2:4].[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:20]=1[N:29]=[C:30]=[O:31]>ClCCCl>[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]=[CH:5][C:3]=1[NH:4][C:30]([NH:29][C:20]1[CH:21]=[C:22]([C:25]([F:26])([F:28])[F:27])[CH:23]=[CH:24][C:19]=1[F:18])=[O:31]

Participants

4

Reactant 2

HCID 27333802-Fluoro-5-(trifluoromethyl)phenyl isocyanateHCID 179061722-Fluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 58696172HCID 58696172, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (7.65 g, 32.3 mmol, 1 eq) in 1,2-dichloroethane (76.5 mL) was added 1-fluoro-2-isocyanato-4-(trifluoromethyl)benzene (4.9 ml, 33.9 mmol, 1.05 eq). The reaction was allowed to stir overnight. White solids precipitated from the reaction mixture and were filtered and washed with hexanes (3×). The solids were dried under vacuum to obtain 8.75 g (61.3% yield) of the desired product. 1H-NMR (DMSO-d6) δ 9.45 (d, J=2.7 Hz, 1H), 9.32 (d, J=2.76 Hz, 1H), 8.63 (dd, J=7.2, 2.2 Hz, 1H), 8.28 (t, J=8.0 Hz, 1H), 7.50-7.34 (m, 4H), 1.27 (s, 12H); MS [M+H]+=443, LCMS RT=4.50 min

Workup

  1. customWhite solids precipitated from the reaction mixture
  2. filtrationwere filtered
  3. washwashed with hexanes (3×)
  4. customThe solids were dried under vacuum

Sources & evidence

ORD record
ord-74ebd21d7fe646e7b66647bb88ac2b93
Source dataset
uspto-grants-2012_03
Patent number
US08133995B2

Reaction notes

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