Boron tribromide → 2-(4-Diethylcarbamoylbenzyl)phenol

HRID 895611Notes

Reaction equation

HRID 895611 reaction equation
[CH2:1]([N:3]([CH2:21][CH3:22])[C:4]([C:6]1[CH:20]=[CH:19][C:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17]C)=[CH:8][CH:7]=1)=[O:5])[CH3:2].B(Br)(Br)Br>ClCCl>[CH2:21]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH:20]=[CH:19][C:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])=[CH:8][CH:7]=1)=[O:5])[CH3:22]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 223806822-(4-Diethylcarbamoylbenzyl)anisole

Product 1

HCID 223807182-(4-Diethylcarbamoylbenzyl)phenolYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The obtained 2-(4-diethylcarbamoylbenzyl)anisole was dissolved in dichloromethane (280 ml), added with boron tribromide (25.0 g) and stirred at room temperature for 3 hours. After the reaction mixture was slowly poured into ice (300 g) with ice cooling to quench the reaction and the layers were separated, the aqueous layer was extracted with dichloromethane (300 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=1:1) to obtain 10.15 g of the title compound. Yield: 79% (for the three steps).

Workup

  1. customto quench
  2. customthe reaction
  3. customthe layers were separated
  4. extractionthe aqueous layer was extracted with dichloromethane (300 ml)
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-4dccb85b7c8e4f088b0ca9b2f90f19f4
Source dataset
uspto-grants-2005_07
Patent number
US06916822B2

Reaction notes

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