Dichloromethane → HCID 59820864, compound

HRID 1642215Notes

Reaction equation

HRID 1642215 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.F[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N+:20]([O-:22])=[O:21].C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>CN(C=O)C>[F:1][C:2]([F:11])([F:12])[O:3][C:4]1[CH:5]=[CH:6][C:7]([O:10][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-:22])=[O:21])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 70015p-(Trifluoromethoxy)phenolHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 59820864HCID 59820864, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(trifluoromethoxy)phenol (1.36 ml, 10.6 mmol), 2-fluoro-1-nitrobenzene (0.74 ml, 7 mmol), potassium carbonate (1.46 g, 10.5 mmol) were mixed together in DMF (4 ml) and heated at reflux for 5 h. Allowed to cool, and evaporated in-vacuo. Residue partitioned between diethyl ether and sodium hydroxide (1 M). Organic layers combined and dried over anhydrous magnesium sulphate and evaporated in-vacuo, to afford a yellow oil, 2.34 g, >100%. Rf: 0.72 (DCM), 1HNMR (CDCl3, 270 MHz) δ 7.03 (3H, m, Ar HD, Ar HF), 7.20 (2H, dd, J=0.9, 10.1 Hz, Ar HE), 7.23 (1H, m, Ar HB), 7.53 (1H, m, Ar HC), 7.97 (1H, dd, J=1.5, 8.2 Hz, Ar HA).

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 h
  3. temperatureAllowed to cool
  4. customevaporated in-vacuo
  5. customResidue partitioned between diethyl ether and sodium hydroxide (1 M)
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customevaporated in-vacuo
  8. customto afford a yellow oil, 2.34 g, >100%

Sources & evidence

ORD record
ord-f6c68a3b8fd64c5ca90d7bd65fd66743
Source dataset
uspto-grants-2012_02
Patent number
US08119627B2

Reaction notes

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