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

HRID 487412Notes

Reaction equation

HRID 487412 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 95.1%

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 mmol), sodium carbonate (16.7 g; 158 mmol), 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 mmol) was then added, followed by tetrakis(triphenylphosphine)palladium (0.3 g; 0.25 mmol) and the mixture heated at 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 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(2H, 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 heated
  3. temperatureat reflux for 3 hours
  4. filtrationthe warm mixture was filtered through diatomaceous earth
  5. customThe organic phase was separated
  6. extractionthe aqueous phase 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-1c8f3f8188b64283aae1ee734d105c53
Source dataset
uspto-grants-1994_03
Patent number
US05294716

Reaction notes

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