Phenyl chloroformate → Phenyl(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate

HRID 1626660Notes

Reaction equation

HRID 1626660 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[B:9]1[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]1)[NH2:5].C([O-])(O)=O.[Na+].Cl[C:24]([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:25]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([NH:5][C:24](=[O:25])[O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:6]=[CH:7][C:8]=1[B:9]1[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 447552073-Fluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 66678788Phenyl(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (3 g, 12.65 mmol) dissolved in dry THF was stirred with NaHCO3 (1.6 g, 19 mmol) and phenyl chloroformate (1.92 mL, 15.20 mmol) at room temperature overnight. The reaction mixture was partitioned between water and DCM, the organic layer recovered, dried over MgSO4, filtered and the solvent removed in vacuo, affording the title compound which was used without further purification.

Workup

  1. customThe reaction mixture was partitioned between water and DCM
  2. customthe organic layer recovered
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-aef33446f0ef4400aebacbe93e7021ef
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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