Sodium Iodide → 4-(3-Benzyloxypropyloxy)-3-(3-methoxypropyloxy)-bromobenzene

HRID 2256726Notes

Reaction equation

HRID 2256726 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([O:9][CH2:10][CH2:11][CH2:12][O:13][CH3:14])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][CH2:23][CH2:24][O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[Na+].[I-]>C(#N)C>[CH2:26]([O:25][CH2:24][CH2:23][CH2:22][O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[O:9][CH2:10][CH2:11][CH2:12][O:13][CH3:14])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 2776064Benzyl 3-Bromopropyl EtherHCID 214586624-Bromo-2-(3-methoxypropoxy)-phenol

Product 1

HCID 214586464-(3-Benzyloxypropyloxy)-3-(3-methoxypropyloxy)-bromobenzene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4 g of 4-bromo-2-(3-methoxypropyloxy)-phenol, 2.3 g of potassium carbonate, 3.8 g of benzyl (3-bromopropyl) ether, a spatula tip of NaI and 15 ml of acetonitrile is stirred under reflux for 30 hours. The reaction mixture is filtered and the filtrate is concentrated by evaporation. The residue is partitioned between ethyl acetate and water. The organic phases are combined, dried over magnesium sulfate and concentrated by evaporation, and the residue is purified by means of FC (hexane/ethyl acetate=95:5), yielding the title compound: Rf (hexane/ethyl acetate=9:1)=0.15; HPLC Rt =20.66 minutes.

Workup

  1. temperatureunder reflux for 30 hours
  2. filtrationThe reaction mixture is filtered
  3. concentrationthe filtrate is concentrated by evaporation
  4. customThe residue is partitioned between ethyl acetate and water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated by evaporation
  7. customthe residue is purified by means of FC (hexane/ethyl acetate=95:5)

Sources & evidence

ORD record
ord-9e35111a13014603b810bb8ad82f04db
Source dataset
uspto-grants-1997_08
Patent number
US05654445

Reaction notes

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