Hydrochloric Acid → HCID 13515581, compound

HRID 1193478Notes

Reaction equation

HRID 1193478 reaction equation
[H-].[Na+].[F:3][C:4]([F:8])([F:7])[CH2:5][OH:6].Cl[C:10]1[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:11]=1[N+:17]([O-:19])=[O:18].Cl>CN(C=O)C.CCCCCC>[Cl:16][C:15]1[C:10]([O:6][CH2:5][C:4]([F:8])([F:7])[F:3])=[C:11]([N+:17]([O-:19])=[O:18])[CH:12]=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 64092,2,2-TrifluoroethanolHCID 185552,3-DichloronitrobenzeneHCID 24758Sodium hydride

Product 1

HCID 13515581HCID 13515581, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8058HexaneSolvent

Procedure

According to the procedure of J. T. Gupton et al, Can. J. Chem. 63, 3037 (1985), a suspension of hexane-washed sodium hydride (8.4 g, 0.21 mol) in DMF (250 mL) was added to 2,2,2-trifluoroethanol (22.1 mL, 0.3 mol) dropwise in 200 mL of DMF at room temperature over 60 minutes (excessive frothing occurs if added too fast). After stirring an additional 30 minutes 2,3-dichloronitrobenzene (38 g, 0.20 mol) was added in one portion. The resulting mixture was stirred at room temperature for 2 hours. The reaction was then poured into 1N HCl (500 mL) and extracted with Et2O (2×500 mL). The combined Et2O layers were washed first with water (200 mL) and finally with saturated brine (200 mL). After drying (MgSO4), the ether was concentrated to yield 47 g (90% based on dichloronitrobenzene) of 3-chloro-2-(2,2,2-trifluoroethoxy)nitrobenzene as a yellow liquid (b.p. 85° C./0.3 mmHg), which was used without further purification.

Workup

  1. additionif added too fast)
  2. additionwas added in one portion
  3. extractionextracted with Et2O (2×500 mL)
  4. washThe combined Et2O layers were washed first with water (200 mL) and finally with saturated brine (200 mL)
  5. dry with materialAfter drying (MgSO4)
  6. concentrationthe ether was concentrated
  7. customto yield 47 g (90% based on dichloronitrobenzene) of 3-chloro-2-(2,2,2-trifluoroethoxy)nitrobenzene as a yellow liquid (b.p. 85° C./0.3 mmHg), which
  8. customwas used without further purification

Sources & evidence

ORD record
ord-10b706892d30404d8a4f4d856c24560a
Source dataset
uspto-grants-1989_03
Patent number
US04810699

Reaction notes

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