Dimethylformamide → HCID 54970610, compound

HRID 2171636Notes

Reaction equation

HRID 2171636 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][OH:9])[CH:5]=[CH:6][CH:7]=1.CN(C=O)C.[H-].[Na+].Cl[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1>CCOC(C)=O.O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][O:9][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH:3]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 851413-Bromobenzyl alcohol

Product 1

HCID 54970610HCID 54970610, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

(3-Bromophenyl)methanol (500 mg) was mixed with DMF (10 ml), and sodium hydride (55% suspended in oil) was added thereto at 0° C., followed by stirring for 10 minutes under ice-cooling. 1-(Chloromethyl)-4-methoxybenzene (520 mg) was added to the reaction mixture, followed by stirring at room temperature for 2 hours. Water and EtOAc were added to the reaction mixture, and the organic layer was dried over MgSO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (CHCl3/hexane) to obtain 1-bromo-3-{[(4-methoxybenzyl)oxy]methyl}benzene (801 mg).

Workup

  1. additionwas added
  2. customat 0° C.
  3. temperaturecooling
  4. stirringby stirring at room temperature for 2 hours
  5. dry with materialthe organic layer was dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (CHCl3/hexane)

Sources & evidence

ORD record
ord-3396e8b74ccb4e9f8c2dcc15a83d41f9
Source dataset
uspto-grants-2015_06
Patent number
US09051283B2

Reaction notes

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