Methanol → HCID 68661512, compound

HRID 2197666Notes

Reaction equation

HRID 2197666 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][C:9]1[O:10][C:11]2[C:16]([C:17](=[O:27])[C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=1)=[C:15]([OH:28])[CH:14]=[C:13]([OH:29])[CH:12]=2)=[O:5])C.B(Br)(Br)Br.CO>C(Cl)Cl>[CH3:1][O:3][C:4]([CH2:6][CH2:7][CH2:8][C:9]1[O:10][C:11]2[C:16]([C:17](=[O:27])[C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)=[C:15]([OH:28])[CH:14]=[C:13]([OH:29])[CH:12]=2)=[O:5]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 68661946HCID 68661946, compound

Product 1

HCID 68661512HCID 68661512, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-[3-(ethoxycarbonyl)propyl]-7,5-dihydroxy-4′-methoxyisoflavone (104 mg, 0.26 mmol), prepared according to Pelter et al. (Pelter et al, 1998) in anhydrous DCM (2 ml) at −78° C. under nitrogen, 1.0 M BBr3 in DCM (2.1 ml, 2.1 mmol) was added slowly. The mixture was allowed to warm gradually to room temperature overnight. The mixture was then cooled in an ice bath and anhydrous MeOH (2 ml) was added slowly. The solvents were evaporated under reduced pressure leaving a brown solid that was purified by column chromatography on silica gel (gradient elution: DCM to DCM/acetone 8:2) yielding 2-[3-(methoxycarbonyl)propyl]-5,7,4′-trihydroxyisoflavone as a solid (72 mg, 75%).

Workup

  1. temperatureThe mixture was then cooled in an ice bath
  2. customThe solvents were evaporated under reduced pressure
  3. customleaving a brown solid that
  4. customwas purified by column chromatography on silica gel (gradient elution: DCM to DCM/acetone 8:2)

Sources & evidence

ORD record
ord-327136c62dd24480b7bd9ced1b658421
Source dataset
uspto-grants-2012_12
Patent number
US08338624B2

Reaction notes

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