Water → HCID 57995656, compound

HRID 385360Notes

Reaction equation

HRID 385360 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].F[C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[C:10](F)[C:9]=1[N+:16]([O-:18])=[O:17].[OH2:19]>C1(C)C=CC=CC=1>[F:14][C:12]1[CH:13]=[C:8]([O:19][CH2:3][C:2]([F:6])([F:5])[F:1])[C:9]([N+:16]([O-:18])=[O:17])=[C:10]([O:4][CH2:3][C:2]([F:6])([F:5])[F:1])[CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 64092,2,2-TrifluoroethanolHCID 675671,3,5-Trifluoro-2-nitrobenzene

Product 1

HCID 57995656HCID 57995656, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of 2,2,2-trifluoroethanol (28.2 g, 282.0 mmol) in toluene (120 mL) n-BuLi (1.6 M in hexane, 8.0 g, 80 mL, 125.0 mmol) was added at 0° C. and the reaction mixture warmed up to 25° C. A solution of 1,3,5-trifluoronitrobenzene (10.0 g, 56.5 mmol) in toluene (50 mL) was added dropwise. The reaction mixture was refluxed for 30 h and then poured into water (100 mL). The reaction mixture was extracted with EtOAc (3×100 mL). The organic layers were combined and dried over MgSO4. The solvent was evaporated under reduced pressure to give 5-fluoro-2-nitro-1,3-bis-(2,2,2-trifluoro-ethoxy)-benzene as a brown oil (18.0 g, 95%). The product was used for the next step without purification. 1H NMR (300 MHz, CDCl3/TMS): δ 6.47 (d, J=9.4 Hz, 2H), 4.40 (q, J=8.0 Hz, 4H).

Workup

  1. temperatureThe reaction mixture was refluxed for 30 h
  2. extractionThe reaction mixture was extracted with EtOAc (3×100 mL)
  3. dry with materialdried over MgSO4
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-26538022f62e4f6b9a26a3a4632e19f0
Source dataset
uspto-grants-2013_02
Patent number
US08367863B2

Reaction notes

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