Water → Tert-butyl phenyl(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)carbamate

HRID 1188302Notes

Reaction equation

HRID 1188302 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[B:9]1[O:17][C:14]([CH3:16])([CH3:15])[C:11]([CH3:13])([CH3:12])[O:10]1.CN(C)C=O.[Li][N:24]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].O>CCOCC>[C:32]1([N:24]([CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[B:9]2[O:17][C:14]([CH3:16])([CH3:15])[C:11]([CH3:13])([CH3:12])[O:10]2)[C:25](=[O:26])[O:27][C:28]([CH3:30])([CH3:29])[CH3:31])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 38348342-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl Bromide2×HCID 178506929HCID 178506929, compound

Product 1

HCID 66795645Tert-butyl phenyl(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)carbamate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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 clear colorless solution
  2. customthe organics were separated
  3. dry with materialdried with brine
  4. filtrationFiltration
  5. customfollowed by evaporation

Sources & evidence

ORD record
ord-d80e352774614a1a8db31bb1822343d4
Source dataset
uspto-grants-2014_03
Patent number
US08674040B2

Reaction notes

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