Potassium Carbonate → HCID 19955441, compound

HRID 2096562Notes

Reaction equation

HRID 2096562 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Cl[CH2:10][CH2:11][CH2:12][O:13][CH3:14].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:10][CH2:11][CH2:12][O:13][CH3:14])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 115633-BromophenolHCID 1189271-Chloro-3-methoxypropane

Product 1

HCID 19955441HCID 19955441, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-bromophenol (5 g, 29 mmol), 1-chloro-3-methoxypropane (4.33 g, 40 mmol) and K2CO3 (8 g, 57.8 mmol) in DMF (90 mL) was stirred at 100° C. for 2 h. the reaction mixture was filtered and the filtrate was evaporated in vacuo. The residue was taken up in t-BuME, and the organic layer was washed with aqueous NaOH (1N), water (50 mL) and brine. The organic layer was dried and concentrated to give 1-bromo-3-(3-methoxypropoxy)benzene (7 g, 99%). 1H-NMR (CDCl3): 2.02 (m, 2H), 3.33 (s, 3H), 3.54 (m, 2H), 4.02 (m, 2H), 6.82 (m, 1H), 7.11 (m, 3H).

Workup

  1. filtrationwas filtered
  2. customthe filtrate was evaporated in vacuo
  3. washthe organic layer was washed with aqueous NaOH (1N), water (50 mL) and brine
  4. customThe organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ac5455a489dc43c0b37fe829a65e88cb
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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