Cesium carbonate → HCID 66665444, compound

HRID 474236Notes

Reaction equation

HRID 474236 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-].[Cs+].[Cs+].Br[CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26]>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 692642-Chloro-5-nitrophenolHCID 4460490tert-butyl N-(3-bromopropyl)carbamate

Product 1

HCID 66665444HCID 66665444, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-chloro-5-nitrophenol (2 g, 11.62 mmol), cesium carbonate (5.66 g, 17.44 mmol) in DMF (20 mL) was added tert-butyl 3-bromopropylcarbamate (4.13 g, 17.44 mmol) followed by tetrabutylammonium iodide (0.214 g, 0.581 mmol) at room temperature. The reaction mixture was stirred at room temperature for 18 h while monitoring by TLC and LC-MS. The solvent was removed under reduced pressure and the residue was taken up in ethyl acetate (200 mL) and washed with brine (2×200 mL). The organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to give tert-butyl 3-(2-chloro-5-nitrophenoxy)propylcarbamate (2.2 g, 57.4%) as a light-brown solid. LC-MS (M−100)+=230.7 1H NMR (400 MHz, CDCl3) δ ppm 7.82-7.76 (2H, m), 7.52 (1H, d, J=8.4 Hz), 4.99 (1H, s), 4.20 (2H, t, J=5.6 Hz), 3.41-3.37 (2H, q, J=6.0 Hz), 2.12-2.01 (2H, m), 1.43 (9H, s).

Workup

  1. customThe solvent was removed under reduced pressure
  2. washwashed with brine (2×200 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0684522dc3354c809fe47be2f17a922a
Source dataset
uspto-grants-2014_01
Patent number
US08637523B2

Reaction notes

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