4-Methoxyphenol → HCID 23450319, compound

HRID 1839464Notes

Reaction equation

HRID 1839464 reaction equation
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1.[N+:16]([C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21]Br)([O-:18])=[O:17]>C1COCC1>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:21][C:20]2[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=2[N+:16]([O-:18])=[O:17])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 90154-MethoxyphenolHCID 77569alpha-Bromo-2-nitrotolueneHCID 23665647Potassium tert-butoxide

Product 1

HCID 23450319HCID 23450319, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of potassium t-butoxide (5.7 g, 51 mmol) in THF (200 mL) was added 4-methoxyphenol (6.3 g, 51 mmol). After 10 min, 2-nitrobenzyl bromide (10 g, 46 mmol) was added. After 48 h, the reaction was concentrated and the residue was dissolved in ethyl acetate, washed with 1 N citric acid (2×), brine, satd aq NaHCO3 (2×), water, and brine. The organic layer was MgSO4 dried, concentrated, triturated with ether, filtered and vacuum dried to give the title compound as an off-white solid (8.4 g, 71%); MS(FD): 259.

Workup

  1. waitAfter 48 h
  2. concentrationthe reaction was concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with 1 N citric acid (2×), brine
  5. customdried
  6. concentrationconcentrated
  7. customtriturated with ether
  8. filtrationfiltered
  9. customvacuum dried

Sources & evidence

ORD record
ord-c7501503f4e4446db06bdd229f147fd4
Source dataset
uspto-grants-2004_01
Patent number
US06677369B2

Reaction notes

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