Hydrochloric Acid → 4-Hexyloxyphenylboronic Acid

HRID 327360Notes

Reaction equation

HRID 327360 reaction equation
[CH2:1]([O:7][C:8]1[CH:13]=[CH:12][C:11](Br)=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[B:15](OC(C)C)([O:20]C(C)C)[O:16]C(C)C.Cl>C1COCC1>[CH2:1]([O:7][C:8]1[CH:13]=[CH:12][C:11]([B:15]([OH:20])[OH:16])=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 520492Benzene, 1-bromo-4-(hexyloxy)-

Product 1

HCID 36821484-Hexyloxyphenylboronic Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the Grignard Reagent prepared from 1A (72 g) and Mg (7.75 g) in dry THF 250 ml) is added dropwise to a stirred, cooled (-78° C.) solution of tri-isopropyl borate (109.1 g) in dry THF 40 ml) under dry N2. The stirred mixture is allowed to warm to room temperature overnight and stirred with 10% HCl (320 ml) at room temperature for 1 hr. The product is extracted into ether twice, and the combined etheral extracts are washed with water and dried (MgSO4). Solvent is removed in vacuo to yield a colourless solid, mp =80°-85° C.

Workup

  1. additionis added dropwise to a stirred
  2. extractionThe product is extracted into ether twice
  3. washthe combined etheral extracts are washed with water
  4. dry with materialdried (MgSO4)
  5. customSolvent is removed in vacuo
  6. customto yield a colourless solid, mp =80°-85° C.

Sources & evidence

ORD record
ord-472786136de14d559bbd9d843e11fbdf
Source dataset
uspto-grants-1993_12
Patent number
US05273680

Reaction notes

Loading…