Hydrochloric Acid → 3,5-Dimethylbiphenyl-4-ylboronic acid

HRID 72279Notes

Reaction equation

HRID 72279 reaction equation
C([Li])(C)(C)C.Br[C:7]1[C:12]([CH3:13])=[CH:11][C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:9][C:8]=1[CH3:20].C[O:22][B:23](OC)[O:24]C.Cl>O1CCCC1>[CH3:13][C:12]1[C:7]([B:23]([OH:24])[OH:22])=[C:8]([CH3:20])[CH:9]=[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 230937004-Bromo-3,5-dimethyl-1,1'-biphenylHCID 178418306HCID 178418306, compound

Product 1

HCID 594504813,5-Dimethylbiphenyl-4-ylboronic 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 4-bromo-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. Trimethylborate (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-dimethylbiphen-4-ylboronic 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-92a65d1e1a054515baea0dcd8007b949
Source dataset
uspto-grants-2014_09
Patent number
US08828908B2

Reaction notes

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