1,3-Dichloro-2-propanol → 1-(2-Chloro-1-chloromethyl-ethoxy)-2-nitro-benzene

HRID 33106Notes

Reaction equation

HRID 33106 reaction equation
[Cl:1][CH2:2][CH:3]([OH:6])[CH2:4][Cl:5].C([N-]C(C)C)(C)C.F[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22]>C1COCC1.O>[Cl:1][CH2:2][CH:3]([CH2:4][Cl:5])[O:6][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22]

Participants

6

Reactant 3

HCID 72891,3-Dichloro-2-propanolHCID 738951-Fluoro-2-nitrobenzeneHCID 5062348Diisopropylamide

Product 1

HCID 597964371-(2-Chloro-1-chloromethyl-ethoxy)-2-nitro-benzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1,3-dichloro-propan-2-ol (1.29 g, 10 mmoles) in THF, under nitrogen, was cooled to 0° C., treated dropwise with llithium diisopropylamide (LDA) (5 ml, 2M solution in hexanes, 10 mmoles), while maintaining the temperature constant at 0° C., stirred at 0° C. for 15 minutes, treated with 1-fluoro-2-nitro-benzene (1.2 g ml, 8.5 mmoles) and stirred at room temperature overnight. The reaction mixture was diluted with water and extracted with EtOAc. The extracts were combined, washed with brine, dried over Na2SO4, and concentrated under vacuum, to afford the title compound as an off-white solid (2.0 g, 8 mmoles), identified by HNMR analysis.

Workup

  1. stirring8.5 mmoles) and stirred at room temperature overnight
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-03aa5ce4606b46f982c303e8feae936c
Source dataset
uspto-grants-2008_09
Patent number
US07429582B2

Reaction notes

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