Hydrochloric Acid → 3,5-Dimethylbiphenylboronic acid

HRID 43330Notes

Reaction equation

HRID 43330 reaction equation
C([Li])(C)(C)C.[CH3:6][C:7]1[CH:8]=[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]=[C:11]([CH3:13])[CH:12]=1.[B:20](OC)([O:23]C)[O:21]C.Cl>O1CCCC1>[CH3:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]=1[B:20]([OH:23])[OH:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 869273,5-DimethylbiphenylHCID 178418306HCID 178418306, compound

Product 1

HCID 666885243,5-Dimethylbiphenylboronic acidYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyllithium (1.7 M solution in hexanes, 36.2 ml, 62.6 mmol) is added dropwise to a solution of 3,5-dimethylbiphenyl (7.27 g; 28 mmol) in dry tetrahydrofuran (150 ml) at −78° C. and stirred under an atmosphere of nitrogen for 30 minutes. Trimethyl borate (9.54 ml; 84 mmol) is added and the resulting mixture is stirred at −78° C. for 30 min and then allowed to warm to room temperature. The reaction mixture is acidified with aqueous hydrochloric acid and extracted with ether (2×150 ml). The organic layers are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated in vacuo to give a yellow solid. The crude product is triturated with iso-hexane and filtered to give 3,5-dimethylbiphenylboronic acid (5.89 g) as a white powder.

Workup

  1. stirringthe resulting mixture is stirred at −78° C. for 30 min
  2. extractionextracted with ether (2×150 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe filtrate evaporated in vacuo
  6. customto give a yellow solid
  7. customThe crude product is triturated with iso-hexane
  8. filtrationfiltered

Sources & evidence

ORD record
ord-3094254536064113a888ccccc095845e
Source dataset
uspto-grants-2013_09
Patent number
US08536351B2

Reaction notes

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