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

HRID 1771528Notes

Reaction equation

HRID 1771528 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]2[O:16][C:13]([CH3:15])([CH3:14])[C:10]([CH3:12])([CH3:11])[O:9]2)=[C:4]([F:17])[CH:3]=1.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>[C:27]1([O:26][C:24](=[O:25])[NH:1][C:2]2[CH:7]=[CH:6][C:5]([B:8]3[O:9][C:10]([CH3:12])([CH3:11])[C:13]([CH3:15])([CH3:14])[O:16]3)=[C:4]([F:17])[CH:3]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=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

To a stirred solution of 4-amino-2-fluorophenyl boronic acid pinacol ester (3.0 g, 12.7 mmol) in THF (10 ml) was added sodium hydrogen carbonate (1.6 g, 19.0 mmol) followed by phenyl chloroformate (1.9 ml, 15.2 mmol) and stirred overnight at room temperature. The reaction mixture was partitioned between DCM and water, the organic phase recovered, dried over Mg2SO4 and filtered before being concentrated in-vacuo to afford a white solid (4.95 g, quantitative).

Workup

  1. customThe reaction mixture was partitioned between DCM and water
  2. customthe organic phase recovered
  3. dry with materialdried over Mg2SO4
  4. filtrationfiltered
  5. concentrationbefore being concentrated in-vacuo
  6. customto afford a white solid (4.95 g, quantitative)

Sources & evidence

ORD record
ord-af7756587b32428eabc2490cf829d01d
Source dataset
uspto-grants-2016_02
Patent number
US09249129B2

Reaction notes

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