1-Bromo-3-chloropropane → HCID 11950718, compound

HRID 251439Notes

Reaction equation

HRID 251439 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:6][O:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)=[N:3]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][CH2:23][CH2:24][Cl:25]>CC(C)=O>[Cl:25][CH2:24][CH2:23][CH2:22][O:13][C:10]1[CH:11]=[CH:12][C:7]([C:4]2[O:5][CH2:6][C:2]([CH3:14])([CH3:1])[N:3]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 1357785094-(4,4-Dimethyl-1,3-oxazolidin-2-ylidene)cyclohexa-2,5-dien-1-one

Product 1

HCID 11950718HCID 11950718, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)phenol ax7 (5 g, 26 mmol, 1 eq), potassium carbonate (7.19 g, 52 mmol, 2 eq), and 1-bromo-3-chloropropane (2.8 ml, 29 mmol, 1.1 eq) in acetone (120 ml) is stirred at reflux for 36 h. The mixture is then concentrated; the residue is dissolved in dichloromethane, and washed with a saturated solution of aqueous ammonium chloride. The organic layer is dried over magnesium sulfate and concentrated under vacuum to obtain 2-[4-(3-chloropropoxy)phenyl]-4,4-dimethyl-4,5-dihydro-1,3-oxazole ax10 as a white solid (6.75 g).

Workup

  1. temperatureat reflux for 36 h
  2. concentrationThe mixture is then concentrated
  3. dissolutionthe residue is dissolved in dichloromethane
  4. washwashed with a saturated solution of aqueous ammonium chloride
  5. dry with materialThe organic layer is dried over magnesium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-451b1a0b3e30443989d749bbd2e8912c
Source dataset
uspto-grants-2011_01
Patent number
US07863450B2

Reaction notes

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