2-Chloro-5-nitrobenzotrifluoride → 3-(Trifluoromethyl)-4-(cyclopropylmethoxy)nitrobenzene

HRID 1862792Notes

Reaction equation

HRID 1862792 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[CH:6]=[CH:7][C:8]=1Cl.[CH:15]1([CH2:18][O-:19])[CH2:17][CH2:16]1.[Na+]>CS(C)=O>[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[CH:6]=[CH:7][C:8]=1[O:19][CH2:18][CH:15]1[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 612132-Chloro-5-nitrobenzotrifluorideHCID 23704981Sodium cyclopropylmethoxide

Product 1

HCID 105633403-(Trifluoromethyl)-4-(cyclopropylmethoxy)nitrobenzeneYield 42.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
10 °C

Procedure

To a cooled (10° C.) solution containing 22.5 g (0.1 mole) of 3-(trifluoromethyl)-4-chloronitrobenzene in 100 ml of DMSO was added with stirring at ambient temperature a solution containing 0.11 mole of sodium cyclopropylmethoxide (prepared by dissolving 4.9 g of 57% sodium hydride in 7.9 g of cyclopropylmethanol and 50 ml of tetrahydrofuran) in 100 ml of DMSO. The reaction mixture was heated at 50° C. for one hour, poured into ice water and filtered. Recrystallization of the filter cake from hexane gave 11.0 g (42%) of product as a white crystalline solid, m.p. 41°-44° C.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated at 50° C. for one hour
  3. filtrationfiltered
  4. customRecrystallization of the filter cake from hexane

Sources & evidence

ORD record
ord-219d078f4e4f470c9a3001df231661a0
Source dataset
uspto-grants-1979_09
Patent number
US04166735

Reaction notes

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