2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 4,4,5,5-Tetramethyl-2-(5-methyl-2-((3-methylpent-4-en-2-yl)oxy)phenyl)-1,3,2-dioxaborolane

HRID 1400758Notes

Reaction equation

HRID 1400758 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[O:9][CH:10]([CH:12]([CH3:15])[CH:13]=[CH2:14])[CH3:11].[Li]CCCC.C1COCC1.C(O[B:30]1[O:34][C:33]([CH3:36])([CH3:35])[C:32]([CH3:38])([CH3:37])[O:31]1)(C)C>C1COCC1>[CH3:37][C:32]1([CH3:38])[C:33]([CH3:36])([CH3:35])[O:34][B:30]([C:2]2[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=2[O:9][CH:10]([CH:12]([CH3:15])[CH:13]=[CH2:14])[CH3:11])[O:31]1

Participants

5

Reactant 3

HCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 867108152-Bromo-4-methyl-1-((3-methylpent-4-en-2-yl)oxy)benzeneHCID 178420697HCID 178420697, compound

Product 1

HCID 867108164,4,5,5-Tetramethyl-2-(5-methyl-2-((3-methylpent-4-en-2-yl)oxy)phenyl)-1,3,2-dioxaborolane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromo-4-methyl-1-((3-methylpent-4-en-2-yl)oxy)benzene (820 mg, 3.05 mmol) in THF (15.200 mL) at −78° C. was added 1.6M n-BuLi/THF (2.285 mL, 3.66 mmol) and the mixture was stirred for 30 min. 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.746 mL, 3.66 mmol) was then added and after 30 min, bath removed and reaction allowed to warm to rt. After 3 h, partitioned between EtOAc and water. EtOAc layer was dried (Na2SO4), filtered and concentrated. Crude was used as-is in the next step without further purification.

Workup

  1. custombath removed
  2. customreaction
  3. waitAfter 3 h
  4. custompartitioned between EtOAc and water
  5. dry with materialEtOAc layer was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customwithout further purification

Sources & evidence

ORD record
ord-486010cc4b8d4356a4e9289b25064c3c
Source dataset
uspto-grants-2014_12
Patent number
US08906929B2

Reaction notes

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