4-Bromoanisole → HCID 19431321, compound

HRID 1077404Notes

Reaction equation

HRID 1077404 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[Mg].[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][C:21]=1[O:22][CH3:23])[C:18](=[O:24])[C:17]([CH3:26])([CH3:25])[CH2:16]2.[NH4+].[Cl-]>C1COCC1>[OH:24][C:18]1([C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=2)[C:19]2[C:15](=[CH:14][C:13]([O:12][CH3:11])=[C:21]([O:22][CH3:23])[CH:20]=2)[CH2:16][C:17]1([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 77304-BromoanisoleHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 10889431HCID 10889431, compound

Product 1

HCID 19431321HCID 19431321, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A small portion of 4-bromoanisole is added to a suspension of magnesium (72 mg, 3 mmol) in 6 ml of anhydrous THF. The mixture is heated at gentle reflux to initiate the reaction, then the remainder of the brominated derivative (0.56 g, 3 mmol), in solution in 5 ml of THF, is added dropwise over the course of 15 min. After reflux for 1 h, the magnesium has been consumed. 5,6-Dimethoxy-2,2-dimethylindan-1-one (0.66 g, 3 mmol) is added in small portions. The solution is stirred for 1 h at room temperature, then heated at reflux for 4 h. 10 ml of saturated aqueous NH4Cl solution are added at 0° C. The mixture is extracted with AcOEt. The organic phases collected are washed with saturated aqueous NaCl solution, dried over MgSO4 and evaporated to give a yellow oil (1.20 g). Purification by chromatography (eluent: AcOEt/hexane=1:5) enables the isolation of the expected product (0.65 g, 66%).

Workup

  1. temperatureThe mixture is heated
  2. temperatureat gentle reflux
  3. customthe reaction
  4. temperatureAfter reflux for 1 h
  5. customthe magnesium has been consumed
  6. temperatureheated
  7. temperatureat reflux for 4 h
  8. extractionThe mixture is extracted with AcOEt
  9. customThe organic phases collected
  10. washare washed with saturated aqueous NaCl solution
  11. dry with materialdried over MgSO4
  12. customevaporated

Sources & evidence

ORD record
ord-faf8e3d5c68c48c5998d0c55c3efa379
Source dataset
uspto-grants-1996_08
Patent number
US05543298

Reaction notes

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