2-Bromoanisole → HCID 18507125, compound

HRID 1355569Notes

Reaction equation

HRID 1355569 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10].[Br:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1>C1COCC1>[Br:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]([C:8]2[CH:7]=[CH:6][CH:5]=[C:4]([O:9][CH3:10])[CH:3]=2)[OH:17])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 113582-BromoanisoleHCID 707414-BromobenzaldehydeHCID 5462224Magnesium

Product 1

HCID 18507125HCID 18507125, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of magnesium (2.4 g, 100 mmmol), in THF (20 mL) at room temperature was added dropwise a solution of bromoanisole (9.1 mL, 71.4 mmol) in THF (30 mL). The reaction mixture was stirred at room temperature for 2 h and at 600C. for 2 h. The mixture was cooled to room temperature and a solution of 4-bromobenzaldehyde (13.2 g, 71.4 mmol) was added over 5 min. The reaction mixture was stirred at room temperature for 3h and was quenched by addition of aqueous saturated ammonium chloride (NH4Cl) (30 mL). The aqueous layer was washed with ether (3x40 mL), dried over Na2SO4 and concentrated. Purification by flash chromatography with hexanes/EtOAc (10 1) afforded 16.95 g of (4-bromo-phenyl)-(3-methoxy-phenyl)-methanol. 1HNMR (400 MHz, CDCl3) δ 7.46-7.41 (comp, 2H), 7.27-7.18 (comp, 3H), 6.916.87 (comp, 2H), 6.816.78 (m, 1H), 5.73 (s, 1H), 3.76 (s, 3H); MS (M+1) 294.2.

Workup

  1. customwas quenched by addition of aqueous saturated ammonium chloride (NH4Cl) (30 mL)
  2. washThe aqueous layer was washed with ether (3x40 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by flash chromatography with hexanes/EtOAc (10 1)

Sources & evidence

ORD record
ord-e538338971404efeac39ac8ff4029a55
Source dataset
uspto-grants-2003_07
Patent number
US06586431B1

Reaction notes

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