Trimethyl borate → HCID 68246409, compound

HRID 589260Notes

Reaction equation

HRID 589260 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][CH:8]=1.C[O:34][B:35](OC)[O:36]C>C1COCC1>[C:27]1([C:13]([C:10]2[CH:11]=[CH:12][C:7]([B:35]([OH:36])[OH:34])=[CH:8][CH:9]=2)=[C:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 8470Trimethyl borateHCID 248822081,1',1''-[2-(4-Bromophenyl)ethene-1,1,2-triyl]tribenzeneHCID 178418339Butyllithium

Product 1

HCID 68246409HCID 68246409, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a 250 mL two-necked round-bottom flask under nitrogen was slowly added n-butyllithium (1.6 M in hexane, 7.5 mL, 12 mmol) and a THF solution (80 mL) of 1-(4-bromophenyl)-1,2,2-triphenylethene (3) (4.11 g, 10 mmol) at −78° C. After stirring for 3 h, 2.4 mL of trimethylborate (20 mmol) was added into the reaction mixture. The mixture was warmed to room temperature and the reaction was terminated by adding hydrochloric acid (2 M, 10 mL) after 12 h. The mixture was then poured into water and extracted with dichloromethane. The organic layer was washed with water and dried over magnesium sulfate. After filtration and solvent evaporation, the residue was purified by silica-gel column chromatography using n-hexane/ethyl acetate as eluent. White solid of 4-(1,2,2-Triphenylvinyl)phenylboronic acid (4) was obtained in 70% yield (2.6 g). 1H NMR (300 MHz, CDCl3), δ (TMS, ppm): 7.88 (d, 2H, J=8.1 Hz), 7.13-7.00 (m, 17H), 4.49 (s, 1H). 13C NMR (75 MHz, CDCl3), δ (TMS, ppm): 148.9, 144.2, 144.1, 144.09, 142.4, 141.4, 135.6, 133.5, 132.0, 131.6, 128.4, 128.3, 127.4, 127.2. HRMS (TOF): m/e 376.2030 (M+, calcd 376.1635).

Workup

  1. customInto a 250 mL two-necked round-bottom flask under nitrogen was slowly added
  2. customat −78° C
  3. customthe reaction was terminated
  4. additionby adding hydrochloric acid (2 M, 10 mL) after 12 h
  5. additionThe mixture was then poured into water
  6. extractionextracted with dichloromethane
  7. washThe organic layer was washed with water
  8. dry with materialdried over magnesium sulfate
  9. filtrationAfter filtration and solvent evaporation
  10. customthe residue was purified by silica-gel column chromatography

Sources & evidence

ORD record
ord-79be3ebbf0aa49299526fee6cff3ed7f
Source dataset
uspto-grants-2016_01
Patent number
US09228949B2

Reaction notes

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