t-Butyl carbanilate → HCID 178506929, compound

HRID 1944832Notes

Reaction equation

HRID 1944832 reaction equation
[C:1]1([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li:15]CCCC>CCCCC>[Li:15][N:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]([O:9][C:10]([CH3:11])([CH3:13])[CH3:12])=[O:14]

Participants

4

Reactant 2

HCID 137930t-Butyl carbanilateHCID 178418339Butyllithium

Product 1

HCID 178506929HCID 178506929, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

Pentane (350 mL) was added to tert-butyl phenylcarbamate (20.81 g, 107.7 mmol) to form a suspension. BuLi (67.3 mL, 107.7 mmol) in hexanes was added dropwise over 1 hour. During the addition a clear solution formed briefly then a white precipitate formed. After the addition was complete the mixture was stirred for 1 hour then the solid was collected on a glass frit, washed with pentane (2×20 mL), and dried under reduced pressure to afford LiN(Boc)Ph (16.6 g, 77.4%). 2-Bromomethylphenyl boronic acid pinacol ester (compound 9) (4.66 g, 15.7 mmol) and N,N-dimethylformamide (DMF) (35 mL) were combined to form a clear colorless solution. Then solid LiN(Boc)Ph (3.13 g, 15.7 mmol) was added in small portions over three minutes. The mixture was stirred for 2 hours then the white suspension was poured into water (250 mL). Et2O (150 mL) was added and the organics were separated, dried with brine then magnesium sulfate. Filtration followed by evaporation afforded the product as a white solid. 1H NMR (CDCl3, 250 MHz): 7.77 (d, 1H), 7.0-7.5 (m, 8H), 5.19 (s, 2H), 1.39 (s, 9H), 1.27 (s, 12H).

Workup

  1. customto form a suspension
  2. additionDuring the addition a clear solution
  3. customformed briefly
  4. customa white precipitate formed
  5. additionAfter the addition
  6. customthe solid was collected on a glass frit
  7. washwashed with pentane (2×20 mL)
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-166b48a73967493fbb5c5107f7af27d7
Source dataset
uspto-grants-2013_03
Patent number
US08394902B2

Reaction notes

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