Hydrochloric Acid → 4-(2-Hydroxyethyl)phenylboronic acid

HRID 1454710Notes

Reaction equation

HRID 1454710 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1.[Li]CCCC.CCCCCC.[B:22](OC(C)C)([O:27]C(C)C)[O:23]C(C)C.Cl>C1COCC1>[OH:8][CH2:7][CH2:6][C:5]1[CH:9]=[CH:10][C:2]([B:22]([OH:27])[OH:23])=[CH:3][CH:4]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 21531Triisopropyl borateHCID 728512-(4-Bromophenyl)ethanolHCID 178418339Butyllithium

Product 1

HCID 101762864-(2-Hydroxyethyl)phenylboronic acidYield 63.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 4-bromophenethylalcohol (5.00 g, 24.9 mmol) in THF (80 ml) was added a solution of 1.5 M n-BuLi in hexane (39.8 ml, 59.7 mmol) at −78° C. over 30 min. After 1 hour, a solution of B(OiPr)3 (8.61 ml, 37.3 mmol) in THF (20 ml) was added slowly to the mixture at −78° C. The resultant mixture was warmed to room temperature, and treated with 2M HCl (100 ml) for 1 hour. This was extracted with CH2Cl2 and dried over MgSO4, then filtered. After evaporation in vacuo, the residue was purified by silica-gel column chromatography eluting with CH2Cl2/MeOH=20/1 to afford 2.61 g (63%) of the title compound.

Workup

  1. extractionThis was extracted with CH2Cl2
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customAfter evaporation in vacuo
  5. customthe residue was purified by silica-gel column chromatography
  6. washeluting with CH2Cl2/MeOH=20/1

Sources & evidence

ORD record
ord-7278e790574348fcb2db16166ccaf382
Source dataset
uspto-grants-2009_01
Patent number
US07479564B2

Reaction notes

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