1-Bromopropane → HCID 67455738, compound

HRID 1713266Notes

Reaction equation

HRID 1713266 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][CH2:31][CH3:32]>CN(C)C=O>[CH2:30]([O:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1)[CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 78401-Bromopropane2×HCID 11430Potassium Carbonate2×HCID 67456175HCID 67456175, compound

Product 1

HCID 67455738HCID 67455738, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl N-(3′-hydroxybiphenyl-4-ylmethyl)carbamate (0.300 g) in N,N-dimethylformamide (2.5 mL) was added potassium carbonate (0.194 g). Then 1-bromopropane (0.119 mL) was added, and the resulting mixture was stirred at room temperature for 9.5 hours. Potassium carbonate (0.180 g) and 1-bromopropane (0.110 mL) were added, and stirring was continued at room temperature for additional 14 hours. The reaction mixture was partitioned between diethyl ether (30 mL) and water (10 mL). The organic layer was washed successively with water (10 mL×2) and brine (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound (0.333 g).

Workup

  1. stirringstirring
  2. waitwas continued at room temperature for additional 14 hours
  3. customThe reaction mixture was partitioned between diethyl ether (30 mL) and water (10 mL)
  4. washThe organic layer was washed successively with water (10 mL×2) and brine (10 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ee2eb82737a6472a960e5e7ddca7e088
Source dataset
uspto-grants-2010_09
Patent number
US07795236B2

Reaction notes

Loading…