1,2-Dichlorobenzene → HCID 19910814, compound

HRID 1534142Notes

Reaction equation

HRID 1534142 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19](=O)[C:20](C3C=CC([N+]([O-])=O)=CC=3)=C(C3C=CC=CC=3)[C:22]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:14][CH:13]=1)([O-:11])=[O:10].Cl[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1Cl>CCCCCC>[N+:9]([C:4]1[CH:5]=[CH:6][C:1]([C:7]2[CH:20]=[C:19]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:18]([C:15]3[CH:16]=[CH:17][C:12]([N+:9]([O-:11])=[O:10])=[CH:13][CH:14]=3)=[C:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:8]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:2][CH:3]=1)([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 72391,2-DichlorobenzeneHCID 10821PhenylacetyleneHCID 537011082,5-Bis(4-nitrophenyl)-3,4-diphenylcyclopenta-2,4-dien-1-one

Product 1

HCID 19910814HCID 19910814, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
180 °C

Procedure

1,4-bis(4-nitrophenyl)-2,3,5-triphenylbenzene was prepared according to the procedure described in L. F., "Organic Experiments", 2nd Ed., 297 (1968). 19.3 grams (0.189 moles) of phenylacetylene, 20.0 grams (0.0362 moles) of 2,5-bis(4-nitrophenyl)-3,4-diphenylcyclopentadienone, a compound of formula (II) where Ar1 and Ar2 are phenyl, and 130 mL of o-dichlorobenzene were stirred at 180° C. for 2 hours. The reaction mixture was cooled, poured into 500 mL of hexane and filtered. The reaction yielded 22.9 grams of 1,4-bis(4-nitrophenyl)-2,3,5-triphenylbenzene, a 66% yield.

Workup

  1. custom1,4-bis(4-nitrophenyl)-2,3,5-triphenylbenzene was prepared
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-8208ce6f177d41b58d05bfe598099cf6
Source dataset
uspto-grants-1992_02
Patent number
US05087691

Reaction notes

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