Benzofuran → Benzo[b]furan-2-yl-(3-bromo-6-fluoro-2-methoxy-phenyl)-methanol

HRID 1983520Notes

Reaction equation

HRID 1983520 reaction equation
C([Li])CCC.[CH:6]1[CH:11]=[C:10]2[CH:12]=[CH:13][O:14][C:9]2=[CH:8][CH:7]=1.[Br:15][C:16]1[C:17]([O:25][CH3:26])=[C:18]([C:21]([F:24])=[CH:22][CH:23]=1)[CH:19]=[O:20].[Cl-].[NH4+]>CCCCCC.O1CCCC1.O>[O:14]1[C:13]([CH:19]([C:18]2[C:21]([F:24])=[CH:22][CH:23]=[C:16]([Br:15])[C:17]=2[O:25][CH3:26])[OH:20])=[CH:12][C:10]2[CH:11]=[CH:6][CH:7]=[CH:8][C:9]1=2

Participants

8

Reactant 4

HCID 9223BenzofuranHCID 25517Ammonium ChlorideHCID 222610733-Bromo-6-fluoro-2-methoxybenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 22261032Benzo[b]furan-2-yl-(3-bromo-6-fluoro-2-methoxy-phenyl)-methanolYield 66.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

In an atmosphere of nitrogen gas, 3.56 ml of a 2.66 M solution of n-butyllithium in hexane was added to a solution of 1.12 g of 2,3-benzofuran in 10 ml tetrahydrofuran at −78° C. After stirring at the same temperature for 10 minutes, the mixture was stirred under ice-cooling for 15 minutes and was then stirred at −78° C. for 8 minutes. Then, a solution of 2 g of 3-bromo-6-fluoro-2-methoxy-benzaldehyde in 3.5 ml tetrahydrofuran was added dropwise at the same temperature. After stirring at the same temperature for 30 minutes, saturated aqueous ammonium chloride solution was added at the same temperature. Water was added at room temperature and the mixture was extracted with diethyl ether for two times. The organic layer was sequentially washed with water and brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography, to give 2 g of the title compound as a yellow oil.

Workup

  1. stirringthe mixture was stirred under ice-
  2. temperaturecooling for 15 minutes
  3. stirringwas then stirred at −78° C. for 8 minutes
  4. stirringAfter stirring at the same temperature for 30 minutes
  5. extractionthe mixture was extracted with diethyl ether for two times
  6. washThe organic layer was sequentially washed with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated
  9. customThe crude product was purified
  10. customseparated by silica gel column chromatography

Sources & evidence

ORD record
ord-dab322c8f20b4b95b6b6116407493ddc
Source dataset
uspto-grants-2009_06
Patent number
US07541376B2

Reaction notes

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