Hydrochloric Acid → HCID 86759746, compound

HRID 2183434Notes

Reaction equation

HRID 2183434 reaction equation
[F:1][C:2]([F:17])([F:16])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.[Cl-].[Cl-].[Cl-].[Al+3].[C:22](Cl)(=[O:24])[CH3:23].Cl>[N+](C1C=CC=CC=1)([O-])=O>[F:1][C:2]([F:16])([F:17])[O:3][C:4]1([C:22](=[O:24])[CH3:23])[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:8][CH2:9]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 108899604-Trifluoromethoxy-biphenyl

Product 1

HCID 86759746HCID 86759746, compound

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 30 g (126 mmol) 4-(trifluoromethoxy)-1,1′-biphenyl and 21 g aluminium trichloride (157 mmol) in 120 ml nitrobenzene are added at a temperature below 20° C. 9.87 g (126 mmol) acetyl chloride. The reaction mixture is stirred for 2 h at 0° C., added to 240 ml ice-water and 42 ml conc. HCl and extracted with ethyl acetate. The organic phase is washed with water and brine and the solvents removed in vacuo. The residue is triturated with petrol ether, filtrated and dried. From the filtrate another batch can be obtained after crystallizing at 4° C. to give overall 23.5 g (66%).

Workup

  1. additionare added at a temperature below 20° C
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water and brine
  4. customthe solvents removed in vacuo
  5. customThe residue is triturated with petrol ether
  6. filtrationfiltrated
  7. customdried
  8. customFrom the filtrate another batch can be obtained
  9. customafter crystallizing at 4° C.
  10. customto give overall 23.5 g (66%)

Sources & evidence

ORD record
ord-3397441bae354d209d5f4068d948b263
Source dataset
uspto-grants-2005_05
Patent number
US06900194B1

Reaction notes

Loading…