Water → 5-(4'-Methyl[1,1'-biphenyl]-2-yl)-1-(4-nitrophenyl)-1H-tetrazole

HRID 1741783Notes

Reaction equation

HRID 1741783 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].O.Br[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[N:29]([C:30]2[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=2)[N:28]=[N:27][N:26]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1.CO>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]2[N:29]([C:30]3[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=3)[N:28]=[N:27][N:26]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 79799Tolylboronic acidHCID 199357905-(2-bromophenyl)-1-(4-nitrophenyl)-1H-tetrazole

Product 1

HCID 199357765-(4'-Methyl[1,1'-biphenyl]-2-yl)-1-(4-nitrophenyl)-1H-tetrazoleYield 90.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

A mixture of 4-methylphenyl boronic acid (9.7 g; 71 mM), sodium carbonate (16.7 g; 158 mM), water (100 mL), methanol (50 mL) and toluene (50 mL) was heated to 60° C. to give a clear solution. Compound C (20.0 g; 55 mM) was then added, followed by tetrakis(triphenylphosphine)palladium (0.3 g; 0.25 mM) and the mixture was heated under reflux for 3 hours. Toluene (30 mL) was added and the warm mixture was filtered through diatomaceous earth. The organic phase was separated and the aqueous phase was extracted with toluene (40 mL). The combined organic phases were evaporated to give a solid which was recrystallised from toluene/petroleum ether (100°-120° C.) (1:1 v/v) to give 5-(4'-methylbiphenyl-2-yl)-1-(4-nitrophenyl)-1H-tetrazole (D)(18.7 g; 90% yield), m.p. 164°-166° C.; NMR (CDCl3): 2.3(3H, s), 6.45(2 H, d), 6.85(4H, m), 7.38(1H, d), 7.65(2H, m), 7.85(1H, d), 8.0(2H, d).

Workup

  1. customto give a clear solution
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 3 hours
  4. filtrationthe warm mixture was filtered through diatomaceous earth
  5. customThe organic phase was separated
  6. extractionthe aqueous phase was extracted with toluene (40 mL)
  7. customThe combined organic phases were evaporated
  8. customto give a solid which
  9. customwas recrystallised from toluene/petroleum ether (100°-120° C.) (1:1 v/v)

Sources & evidence

ORD record
ord-f4445d811d0a42898614ec74bb986992
Source dataset
uspto-grants-1994_08
Patent number
US05334718

Reaction notes

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