Hydrochloric Acid → HCID 67329358, compound

HRID 1257559Notes

Reaction equation

HRID 1257559 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:4][C:3]=1[CH3:12].C([Li])CCC.[B:18](OC(C)C)([O:23]C(C)C)[O:19]C(C)C.Cl>O1CCCC1.CCCCCC>[CH3:12][C:3]1[CH:4]=[C:5]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:6]=[CH:7][C:2]=1[B:18]([OH:23])[OH:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 58745545HCID 58745545, compoundHCID 178418339Butyllithium

Product 1

HCID 67329358HCID 67329358, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-5 °C

Procedure

The obtained 1-bromo-2-methyl-4-(t-butyl)benzene (10.70 g, 47.1 mmol) was dissolved in tetrahydrofuran (50 mL). After cooling at −5° C., solution of n-butyllithium in n-hexane (1.65 M, 31.40 mL) was dropped, and reaction solution was stirred for 1 hour, then, triisopropyl borate (14.10 mL, 61.3 mmol) was dropped, and stirred for 1 hour. Temperature was elevated up to room temperature, then, reaction solution was stirred for 1 hour, then, hydrochloric acid (0.5 M, 30 mL) was added, and reaction solution was stirred for 3 hours. Resulting solid was filtered, and dried under reduced pressure to obtain the desired 2-methyl-4-(t-butyl)phenylboronic acid (7.00 g, 36.4 mmol).

Workup

  1. customreaction solution
  2. stirringstirred for 1 hour
  3. customwas elevated up to room temperature
  4. customreaction solution
  5. stirringwas stirred for 1 hour
  6. customreaction solution
  7. stirringwas stirred for 3 hours
  8. customResulting solid
  9. filtrationwas filtered
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-6d51454ecde6446b926282258dddf736
Source dataset
uspto-grants-2013_06
Patent number
US08461365B2

Reaction notes

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