1,3-Dibromopropane → [4-(3-Bromopropoxy)-5-chloro-2-methoxyphenyl]methanol

HRID 630399Notes

Reaction equation

HRID 630399 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[OH:12].[Br:13][CH2:14][CH2:15][CH2:16]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:13][CH2:14][CH2:15][CH2:16][O:12][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([CH2:8][OH:9])=[C:5]([O:10][CH3:11])[CH:4]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 671453092-Chloro-4-(hydroxymethyl)-5-methoxyphenol2×

Product 1

HCID 67145252[4-(3-Bromopropoxy)-5-chloro-2-methoxyphenyl]methanolYield 80%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 2-chloro-4-(hydroxymethyl)-5-methoxyphenol (intermediate 54; 0.5 g, 2.61 mmol), 1,3-dibromopropane (1.61 ml; 15.71 mmol) and potassium carbonate (737 mg; 5.23 mmol) in 12 ml acetone was heated to 75° C. in a sealed vessel and stirred for 16 hr. The solids were filtered and washed with acetone and the combined filtrates were concentrated to dryness and purified by preparative reversed-phase HPLC (hexane/EtOAc from 0 to 40%), affording the title compound (80%) as a light yellow oil.

Workup

  1. filtrationThe solids were filtered
  2. washwashed with acetone
  3. concentrationthe combined filtrates were concentrated to dryness
  4. custompurified by preparative reversed-phase HPLC (hexane/EtOAc from 0 to 40%)

Sources & evidence

ORD record
ord-89afee8962d64fa1b77581f89eb4169c
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

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