Ammonium Chloride → 5-Bromo-2,3-dihydro-1-benzofuran

HRID 1625867Notes

Reaction equation

HRID 1625867 reaction equation
[Br:1][C:2]1[CH:10]=[C:9](Br)[C:5]2[O:6][CH2:7][CH2:8][C:4]=2[CH:3]=1.C([Li])CCC.[Cl-].[NH4+]>C(OCC)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]2[O:6][CH2:7][CH2:8][C:4]=2[CH:3]=1

Participants

5

Procedure

5,7-Dibromo-2,3-dihydrobenzo[b]furan (see WO 02/070020) (3.0 g) in diethyl ether was cooled to −78° C. under argon atmosphere, and thereto was added dropwise n-butyl lithium (2.44 M hexane solution, 5.09 ml). The mixture was stirred at the same temperature for 30 minutes, and poured into a saturated aqueous ammonium chloride solution. The mixture was extracted with diethyl ether, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give 5-bromo-2,3-dihydrobenzo[b]furan (2.0 g) as pale yellow crystals, which was used in the subsequent step without further purification.

Workup

  1. extractionThe mixture was extracted with diethyl ether
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f8cebef5cad44beab38126a228da36c9
Source dataset
uspto-grants-2014_07
Patent number
US08785403B2

Reaction notes

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