Dimethylformamide → HCID 21182503, compound

HRID 1386606Notes

Reaction equation

HRID 1386606 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1.CN(C)[CH:26]=[O:27].O1CCCC1.C(OCC)(=O)C>C[O-].[Na+].O>[CH3:26][O:27][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 21182552HCID 21182552, compound

Product 1

HCID 21182503HCID 21182503, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10942334Sodium MethoxideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 4-[4-(8-Bromooctyloxy)phenyl]bromobenzene (3.7 g) in a mixture of sodium methoxide (4.9M in methanol, 17 ml), N,N-dimethylformamide (20 ml) and tetrahydrofuran (8 ml) was heated to 80° C. for 3 hours. The reaction mixture was taken up into a mixture of ethyl acetate (200 ml) and water (100 ml). The separated organic layer was washed in turn with water, brine, dried over magnesium sulfate. Evaporation gave a residue which was subjected to column chromatography (silica gel, 100 ml) eluting with n-hexane to give 4-[4-(8-Methoxyoctyloxy)phenyl]bromobenzene (2.73 g).

Workup

  1. washThe separated organic layer was washed in turn with water, brine
  2. dry with materialdried over magnesium sulfate
  3. customEvaporation
  4. customgave a residue which
  5. washeluting with n-hexane

Sources & evidence

ORD record
ord-608291f81c634900b7327d52eea217af
Source dataset
uspto-grants-2001_07
Patent number
US06265536B1

Reaction notes

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