Water → HCID 86666325, compound

HRID 1026352Notes

Reaction equation

HRID 1026352 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([N:12]([O:14][CH3:15])[CH3:13])=[O:11].[H-].[Na+].Br[CH2:19][O:20][CH3:21].O>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH2:19][O:20][CH3:21])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([N:12]([O:14][CH3:15])[CH3:13])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 83093Bromomethyl methyl etherHCID 86666324HCID 86666324, compound

Product 1

HCID 86666325HCID 86666325, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(2-bromo-4-hydroxyphenyl)-N-methoxy-N-methylacetamide (1.37 g) in THF (5 mL) was slowly added to a suspension of sodium hydride (0.22 g) in THF (30 mL) at 0° C. After stirring for 10 min, bromo(methoxy)methane (1.25 g) was added dropwise at 0° C. The mixture was stirred at 0° C. for 2 hr. The mixture was poured into water and extracted with ethyl acetate (30 mL×3). The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated to dryness. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate) to afford the title compound (1.34 g).

Workup

  1. stirringThe mixture was stirred at 0° C. for 2 hr
  2. extractionextracted with ethyl acetate (30 mL×3)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate)

Sources & evidence

ORD record
ord-b827ec374e444c709dce84ddec7bc818
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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