Sodium hydride → 1-((4-Methoxybenzyloxy)methyl)-4-bromobenzene

HRID 9237

Reaction equation

HRID 9237 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][CH:15]=1.[NH4+].[Cl-]>C1COCC1.CN(C=O)C>[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][O:7][CH2:6][C:5]2[CH:8]=[CH:9][C:2]([Br:1])=[CH:3][CH:4]=2)=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 699934-Methyloxybenzyl chlorideHCID 701194-Bromobenzyl alcohol

Product 1

HCID 549706091-((4-Methoxybenzyloxy)methyl)-4-bromobenzeneYield 98%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-bromobenzyl alcohol (2.011 g, 10.7 mmol) in THF (42 mL) was added to a mixture of NaH (663 mg, 16.6 mmol, 60% in oil) in DMF (13 mL). The mixture was stirred for 1.5 h and 4-methoxybenzyl chloride (MPMCl, 2 mL, 14.8 mmol) was added. After 24 h, 100 mL saturated NH4Cl solution was added. The resulting mixture was extracted with ethyl acetate (3×60 mL) and the combined ethyl acetate solution was washed with water and brine. The solution was then dried (Na2SO4), filtered and evaporated. Purification of the residue by flash chromatography on silica gel (5% ethyl acetate/hexanes) gave 7-2 (2.43 g, 98%).

Workup

  1. waitAfter 24 h
  2. extractionThe resulting mixture was extracted with ethyl acetate (3×60 mL)
  3. washthe combined ethyl acetate solution was washed with water and brine
  4. dry with materialThe solution was then dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customPurification of the residue by flash chromatography on silica gel (5% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-505d8cde1f644863b63884fad5906a16
Source dataset
uspto-grants-2006_08
Patent number
US07091231B2

Linked notes

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