Allyl bromide → HCID 12881930, compound

HRID 474225Notes

Reaction equation

HRID 474225 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].C([O-])([O-])=O.[K+].[K+].[CH2:18](Br)[CH:19]=[CH2:20]>CN(C=O)C>[CH2:20]([O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[Cl:1])[CH:19]=[CH2:18]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 692642-Chloro-5-nitrophenol

Product 1

HCID 12881930HCID 12881930, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2-chloro-5-nitrophenol (13.0 g, 75.1 mmol) in DMF (150 mL) was added K2CO3 (15.5 g, 113 mmol). The mixture was cooled to 0° C., and allyl bromide (9.60 mL, 113 mmol) was added dropwise. The reaction was then allowed to stir overnight at rt under nitrogen. The reaction was concentrated to remove DMF, then EtOAc was added to the residue. The mixture was washed with water and brine. The organic layer was dried (Na2SO4), and concentrated in vacuo to afford the highly yellow solid 2-(allyloxy)-1-chloro-4-nitrobenzene (11.5 g, 72% yield). LC-MS (M+H)+212.2. 1H NMR (400 MHz, CDCl3) δ ppm 7.81-7.77 (2H, m), 7.52 (1H, d, J=8.8 Hz), 6.12-6.02 (1H, m), 5.54-5.37 (2H, m), 4.72-4.70 (2H, m).

Workup

  1. concentrationThe reaction was concentrated
  2. customto remove DMF
  3. additionEtOAc was added to the residue
  4. washThe mixture was washed with water and brine
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6eff5c57af0b4d0a97f3bb55afcdf307
Source dataset
uspto-grants-2014_01
Patent number
US08637523B2

Reaction notes

Loading…