O-Xylene → HCID 20089846, compound

HRID 1085930Notes

Reaction equation

HRID 1085930 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[C:13]([F:16])([F:15])[F:14])[C:9](=[O:17])[CH:8]=[CH:7][C:6]2=[O:18].Br[CH:22]1[C:25]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:24]2[CH:23]1Br.BrC1C2=CC=CC=C2C1I.C1(C)C(C)=CC=CC=1>O>[F:1][C:2]([F:19])([F:20])[C:3]1[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][C:10]2[C:9](=[O:17])[C:8]3[C:7](=[CH:23][C:24]4[C:25]([CH:22]=3)=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:6](=[O:18])[C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 7237O-XyleneHCID 568432HCID 568432, compoundHCID 5684347,8-Dibromobicyclo[4.2.0]octa-1,3,5-trieneHCID 20059337HCID 20059337, compound

Product 1

HCID 20089846HCID 20089846, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

25 mmol of 6,7-bis-trifluoromethyl-1,4-naphthquinone, approx. 37 mmol of 1,2-dibromobenzocyclobutene [see J. Am. Chem. Soc. 79, pages 1701 et seq. (1957)] containing a little 1-bromo-2-iodobenzocyclobutene and 100 ml of xylene are kept under reflux for 16 hours in a water separator. The reaction mixture is cooled and the precipitate is filtered off and washed with xylene. The crystalline 2,3-di-(trifluoromethyl)-naphthacene-5,12-dione is obtained in a yield of 5.82 g (71%), melting point>280° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationthe precipitate is filtered off
  3. washwashed with xylene

Sources & evidence

ORD record
ord-46a93b17d6a64a4e8bf486c845bf92a7
Source dataset
uspto-grants-1991_04
Patent number
US05011944

Reaction notes

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