Dimethylformamide → 2-(3-bromopropoxy)-1-chloro-4-nitrobenzene

HRID 330789Notes

Reaction equation

HRID 330789 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4]Br.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:19]=1[OH:27]>O>[Br:1][CH2:2][CH2:3][CH2:4][O:27][C:19]1[CH:20]=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=[CH:23][C:18]=1[Cl:17]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 80011,3-DibromopropaneHCID 10796Cesium carbonateHCID 692642-Chloro-5-nitrophenol

Product 1

HCID 3099122-(3-bromopropoxy)-1-chloro-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,3-dibromo propane (1.3 mL, 12.65 mmol) and cesium carbonate (4.1 g, 12.65 mmol) was added to the DMF (18 mL) solution of 2-chloro-5-nitro phenol (2.0 g, 11.5 mmol) and the reaction mixture stirred overnight at room temperature. Water (20 mL) was added to the mixture, extracted with DCM (3×25 mL) and combined extracts were dried over sodium sulfate and concentrated in vacuo. The crude product was purified by flash column chromatography to get the title compound 26a in 64% (2.176 g) yield as colorless oil.

Workup

  1. extractionextracted with DCM (3×25 mL)
  2. dry with materialwere dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-ca55bf9e3b044887b9543c13b442237c
Source dataset
uspto-grants-2014_11
Patent number
US08877752B2

Reaction notes

Loading…