Hydrochloric Acid → HCID 10738661, compound

HRID 2369635Notes

Reaction equation

HRID 2369635 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.[B:32](OC)([O:35]C)[O:33]C.Cl>O1CCCC1>[CH2:20]([O:19][C:16]1[CH:17]=[CH:18][C:13]([C:10]2[CH:11]=[CH:12][C:7]([B:32]([OH:35])[OH:33])=[CH:8][CH:9]=2)=[CH:14][CH:15]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 64257941,1'-Biphenyl, 4-bromo-4'-(dodecyloxy)-HCID 178418339Butyllithium

Product 1

HCID 10738661HCID 10738661, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Butyllithium (6 ml, 1.6 M in hexanes, 9.6 mmol) was added dropwise to a solution of 4-bromo-4′-(dodecyloxy)biphenyl (4 g, 9.6 mmol) in THF (tetrahydrofuran) (150 mL) under N2 at −78° C. with stirring. Stirring was continued for 1 h and trimethyl borate (3 g, 28.8 mmol) was added. The resulting mixture was warmed to room temperature overnight, acidified with HCl (2 M, 100 mL), extracted with EtOAc (3×200 ml), dried (MgSO4) and the solvent removed under reduced pressure. The residue was filtered through a short plug of silica using EtOAc (0-100% gradient in DCM) as eluent. The solvent was removed under reduced pressure and the residue washed with hexane to give the title compound (0.84 g, 23%) as a colourless powder.

Workup

  1. stirringStirring
  2. extractionextracted with EtOAc (3×200 ml)
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed under reduced pressure
  5. filtrationThe residue was filtered through a short plug of silica
  6. customThe solvent was removed under reduced pressure
  7. washthe residue washed with hexane

Sources & evidence

ORD record
ord-18008ea658884051b38cfe01b01d9977
Source dataset
uspto-grants-2014_04
Patent number
US08703978B2

Reaction notes

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