O-Xylene → HCID 20089836, compound

HRID 1196141Notes

Reaction equation

HRID 1196141 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH:8]=[CH:7][C:6]2=[O:14].Br[CH:18]1[C:21]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:20]2[CH:19]1Br.C1(C)C(C)=CC=CC=1>O>[F:1][C:2]([F:15])([F:16])[C:3]1[CH:12]=[CH:11][C:10]2[C:9](=[O:13])[C:8]3[C:7](=[CH:19][C:20]4[C:21]([CH:18]=3)=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:6](=[O:14])[C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 5684347,8-Dibromobicyclo[4.2.0]octa-1,3,5-trieneHCID 20089837HCID 20089837, compound

Product 1

HCID 20089836HCID 20089836, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.65 g (25 mmol) of 6-(trifluoromethyl)-1,4-naphthoquinone, 9.82 g (about 37 mmol) of 1,2-dibromobenzocyclobutene (contaminated with a little 2-bromo-1-iodobenocyclobutene) and 100 ml of xylene are kept under reflux for 16 hours, using a water separator. The mixture is cooled and the precipitate is filtered off and washed with xylene. Yield 5.82 g (71%); melting point 253°-254° C. The procedure in Examples 58 to 61 is analogous.

Workup

  1. temperatureunder reflux for 16 hours
  2. temperatureThe mixture is cooled
  3. filtrationthe precipitate is filtered off
  4. washwashed with xylene

Sources & evidence

ORD record
ord-4f4b43d18fe24a21a9c2c5d7e75a1dce
Source dataset
uspto-grants-1992_05
Patent number
US05112977

Reaction notes

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