Cyanuric chloride → 2-(4-Biphenylyl)-4,6-dichloro-1,3,5-triazine

HRID 1857944Notes

Reaction equation

HRID 1857944 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([Mg]Br)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:15]1[C:22]([Cl:23])=[N:21][C:19](Cl)=[N:18][C:16]=1[Cl:17]>C1C=CC=CC=1>[C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:12]=[CH:11][C:10]([C:19]2[N:21]=[C:22]([Cl:23])[N:15]=[C:16]([Cl:17])[N:18]=2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 7954Cyanuric chlorideHCID 178419618HCID 178419618, compound

Product 1

HCID 223522432-(4-Biphenylyl)-4,6-dichloro-1,3,5-triazineYield 43%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-phenyl-phenyl magnesium bromide (prepared from 4-bromobiphenyl (7.75 g, 33 mmol) and magnesium turnings (0.83 g, 35 mmol) in 40 mL ether) and cyanuric chloride (4.00 g, 21.7 mmol) in benzene (90 mL) was stirred at 0° C. for 90 minutes. The reaction was evaporated to dryness, and the residue was flash chromatographed on silica gel with 50% hexanes/methylene chloride to provide the desired compound (2.80 g, 43%).

Workup

  1. customThe reaction was evaporated to dryness
  2. customchromatographed on silica gel with 50% hexanes/methylene chloride

Sources & evidence

ORD record
ord-5378414d1feb463ebda5f276a9804101
Source dataset
uspto-grants-2000_11
Patent number
US06150362

Reaction notes

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