Trimethyl borate → (6-Isopropyldibenzo[b,d]furan-4-yl)boronic acid

HRID 717993Notes

Reaction equation

HRID 717993 reaction equation
C([Li])CCC.[CH:6]([C:9]1[C:14]2[O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:13]=2[CH:12]=[CH:11][CH:10]=1)([CH3:8])[CH3:7].[B:22](OC)([O:25]C)[O:23]C.[NH4+].[OH-]>C1COCC1>[CH:6]([C:9]1[C:14]2[O:15][C:16]3[C:21]([B:22]([OH:25])[OH:23])=[CH:20][CH:19]=[CH:18][C:17]=3[C:13]=2[CH:12]=[CH:11][CH:10]=1)([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 8470Trimethyl borateHCID 14923Ammonium HydroxideHCID 156919904-Isopropyldibenzo[b,d]furanHCID 178418339Butyllithium

Product 1

HCID 86684644(6-Isopropyldibenzo[b,d]furan-4-yl)boronic acidYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyl lithium (81 mL, 130 mmol) was added slowly to 4-isopropyldibenzo[b,d]furan (10.9 g, 51.8 mmol) in 100 mL dry THF at −78° C. This mixture was allowed to stir at room temperature for 5 hours and then cooled back to −78° C. Trimethyl borate (20.23 mL, 181 mmol) was added slowly to the reaction and the reaction allowed to warm up to room temperature overnight. The reaction was poured into 100 mL NH4OH solution with ice. The mixture was extracted with 3×100 mL ethyl acetate, dried over sodium sulfate, evaporated and crystallized from DCM/hexane to yield 10.1 g (77%) of the desired product, which was confirmed by NMR.

Workup

  1. temperaturecooled back to −78° C
  2. temperatureto warm up to room temperature overnight
  3. extractionThe mixture was extracted with 3×100 mL ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customcrystallized from DCM/hexane

Sources & evidence

ORD record
ord-1de2f35b0328450f8742329981e85153
Source dataset
uspto-grants-2015_11
Patent number
US09193745B2

Reaction notes

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