Hydrochloric Acid → HCID 60925538, compound

HRID 1714816Notes

Reaction equation

HRID 1714816 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][CH2:15][CH2:16][O:17][CH3:18])[CH:8]=1.[B:19](OC(C)C)([O:24]C(C)C)[O:20]C(C)C.Cl>O1CCCC1>[CH3:18][O:17][CH2:16][CH2:15][CH2:14][O:13][C:9]1[CH:8]=[C:7]([B:19]([OH:24])[OH:20])[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 21531Triisopropyl borateHCID 19955441HCID 19955441, compoundHCID 178418339Butyllithium

Product 1

HCID 60925538HCID 60925538, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.71 ml of n-butyllithium solution (1.6M in hexane) are added dropwise to a solution of 2.5 g of 1 -bromo-3-(3-methoxypropoxy)benzene in 14 ml of dry tetrahydrofuran at −78° C. After stirring at this temperature for 15 minutes, 2.78 ml of triisopropyl borate are added, and the mixture is then slowly warmed to room temperature, 20 ml of 1N ,HCl and 5 ml of conc. HCl are added to the reaction mixture, and the organic solvents are evaporated off in vacuo. The precipitate which has separated out is filtered off with suction and washed twice with ice-water. Drying under high vacuum affords 0.987 g of the title compound as a yellowish brown solid. Rt=3.04.

Workup

  1. customthe organic solvents are evaporated off in vacuo
  2. customThe precipitate which has separated out
  3. filtrationis filtered off with suction
  4. washwashed twice with ice-water
  5. customDrying under high vacuum

Sources & evidence

ORD record
ord-b843d94a1eff4feaabed79e670c69c96
Source dataset
uspto-grants-2010_09
Patent number
US07799779B2

Reaction notes

Loading…