2-Bromoanisole → HCID 18925375, compound

HRID 1289053Notes

Reaction equation

HRID 1289053 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].C([Li])CCC.[C:15]([C:18]1[O:22][CH:21]=[N:20][C:19]=1[CH3:23])(=[O:17])[CH3:16].C(=O)([O-])O.[Na+]>C(OCC)C>[CH3:9][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:15]([C:18]1[O:22][CH:21]=[N:20][C:19]=1[CH3:23])([OH:17])[CH3:16]

Participants

6

Reactant 4

HCID 113582-BromoanisoleHCID 516892Sodium BicarbonateHCID 110298391-(4-Methyloxazol-5-yl)ethanoneHCID 178418339Butyllithium

Product 1

HCID 18925375HCID 18925375, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

2-Bromoanisole (4.86g) in anhydrous diethylether (10 ml) was added dropwise to a stirred solution of n-butyllithium (2.5M solution in hexane, 10.4 ml) in diethylether (30 ml) at -70° C. under an atmosphere of dry nitrogen. After 45 minutes, 5-acetyl-4-methyloxazole (2.5g) in diethylether (loml) was added dropwise. After a further 1 hour at -70° C. the reaction mixture was allowed to warm to room temperature and was stirred overnight. Saturated aqueous sodium hydrogen carbonate was added. The organic layer was separated and the aqueous layer was extracted with diethylether. The combined organic layers were further processed to give the title compound as a white solid, m.p. 74-75° C.

Workup

  1. waitAfter a further 1 hour at -70° C. the reaction mixture was allowed
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with diethylether

Sources & evidence

ORD record
ord-d5efcd2bd8d044f198928888d85169ae
Source dataset
uspto-grants-1998_05
Patent number
US05747515

Reaction notes

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