4-Bromoanisole → HCID 68996244, compound

HRID 750100Notes

Reaction equation

HRID 750100 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[Li]CCCC.[C:15]1([C:21]2[S:25][C:24]([CH:26]=[O:27])=[CH:23][CH:22]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH:26]([C:24]2[S:25][C:21]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:22][CH:23]=2)[OH:27])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 77304-BromoanisoleHCID 1770535-Phenylthiophene-2-carbaldehydeHCID 178418339Butyllithium

Product 1

HCID 68996244HCID 68996244, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromoanisole (0.6 g, 3.2 mmol) in THF was added n-BuLi (2.5M in hexane, 1.5 mL, 3.5 mmol) at −78° C., and continued to stir for 30 min. The product of step 1 (0.48 g, 2.6 mmol) was added. After it was stirred at −78° C. for 30 min, the reaction was allowed to warm to room temperature and stirred for an additional 1 h. The reaction was quenched with water, extracted with EtOAc, washed with brine and dried over Na2SO4. After the solvent was removed, the residue was purified by a column chromatography on silica gel to yield the title compound (0.6 g, 68%).

Workup

  1. stirringAfter it was stirred at −78° C. for 30 min
  2. stirringstirred for an additional 1 h
  3. customThe reaction was quenched with water
  4. extractionextracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customAfter the solvent was removed
  8. customthe residue was purified by a column chromatography on silica gel

Sources & evidence

ORD record
ord-936dcd73e7bd4e7a80e286a0ac3ee597
Source dataset
uspto-grants-2008_07
Patent number
US07402684B2

Reaction notes

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