Hydrochloric Acid → 2-[(1-tert-Butyl)-1H-tetrazol-5-yl]phenylboronic acid

HRID 1886063Notes

Reaction equation

HRID 1886063 reaction equation
[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2Br)=[N:8][N:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].BrCCBr.[B:21](OC(C)C)([O:26]C(C)C)[O:22]C(C)C.Cl>C1COCC1>[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[B:21]([OH:26])[OH:22])=[N:8][N:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 78391,2-DibromoethaneHCID 21531Triisopropyl borateHCID 218408841-tert-Butyl-5-(2-bromophenyl)-1H-tetrazole

Product 1

HCID 109447112-[(1-tert-Butyl)-1H-tetrazol-5-yl]phenylboronic acidYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To dry Mg turnings (76 mg, 3.13 mmol) in THF (1 mL) was added a solution of 1-tert-butyl-5-(2-bromophenyl)-1H-tetrazol (733 mg, 2.61 mmol) in THF (1.5 mL). 1,2-Dibromoethane (20 μL) was added and the mixture was warmed slightly with a heat gun. After 5 min, triisopropyl borate (564 mg, 3.00 mmol) was added and the mixture was stirred at room temperature for 23 h. Ice and and 0.5N HCl (7 mL) were added and the mixture was stirred at for 5 min. The mixture was extracted with ether, and the combined extracts were extracted with 1N KOH (10 mL). The aqueous extracts were filtered and acidified to pH 3 with 2N HCl. The precipitate was collected by filtration to give 306 mg (48%) of product as an off-white solid, mp 112°-115° C.

Workup

  1. temperaturethe mixture was warmed slightly with a heat gun
  2. stirringthe mixture was stirred at for 5 min
  3. extractionThe mixture was extracted with ether
  4. extractionthe combined extracts were extracted with 1N KOH (10 mL)
  5. filtrationThe aqueous extracts were filtered
  6. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-634f8f1382f24309bef36b6fda05dc01
Source dataset
uspto-grants-1992_09
Patent number
US05149699

Reaction notes

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