Isopropenyl chloroformate → Prop-1-en-2-yl 2-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate

HRID 400554Notes

Reaction equation

HRID 400554 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:6]([B:10]2[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]2)=[CH:5][C:3]=1[NH2:4].Cl[C:20]([O:22][C:23]([CH3:25])=[CH2:24])=[O:21]>CCOC(C)=O.C([O-])(O)=O.[Na+]>[F:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:6]([B:10]2[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]2)=[CH:5][C:3]=1[NH:4][C:20](=[O:21])[O:22][C:23]([CH3:25])=[CH2:24]

Participants

5

Reactant 2

HCID 93846Isopropenyl chloroformateHCID 690365482-Fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 86697010Prop-1-en-2-yl 2-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamateYield 100%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Add 2-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (5.0 g, 19.91 mmol) and isopropenyl chloroformate (2.40 mL, 21.90 mmol) in EtOAc (60 mL) and saturated aqueous NaHCO3 (60 mL) and stir at RT for 6 h. Separate the layers, extract the aqueous layer with EtOAc (2×), wash the combined organics with brine, dry over Na2SO4 and concentrate to obtain the title compound. Use for the next reaction without further purification (assuming 100% yield). MS (m/z): 336.2 (M+1).

Workup

  1. customSeparate the layers
  2. extractionextract the aqueous layer with EtOAc (2×)
  3. washwash the combined organics with brine
  4. dry with materialdry over Na2SO4
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-1601dde0404a4dafab00d350f2fb9f74
Source dataset
uspto-grants-2014_06
Patent number
US08741911B2

Reaction notes

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