2-Bromophenol → HCID 19089580, compound

HRID 1463179Notes

Reaction equation

HRID 1463179 reaction equation
Br[CH2:2][C:3]1[C:4]([C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:6]=[CH:7][CH:8]=1.[Br:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20].C(=O)([O-])[O-].[K+].[K+].CCCCCC.C(OCC)(=O)C>CN(C)C=O>[Br:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([O:11][CH3:12])=[O:10]

Participants

6

Reactant 4

HCID 72442-BromophenolHCID 11430Potassium CarbonateHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 21226206Ethyl acetate hexane

Product 1

HCID 19089580HCID 19089580, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl α-bromo-2-toluate (53 g, 0.23 mole) was added to a mixture of 2-bromophenol (40 g, 0.23 mole) and potassium carbonate (42 g, 0.3 mole) in 250 mL of N,N-dimethylformamide. The reaction mixture was stirred at room temperature for 18 hours, then heated on a steam bath for 3.5 hours. The mixture was poured into ice water, and the solids were collected by filtration and washed with water to give the crude product. An analytical sample was obtained by recrystallization from hexane/ethyl acetate (38 g, mp 73°-74° C. pmr (CDCl3) δ: 6.58-8.05 (m, 8, aromatic H); 5.48 (s, 2H, ArCH2O); 3.80 (s, 3H, CO2CH3)

Workup

  1. temperatureheated on a steam bath for 3.5 hours
  2. filtrationthe solids were collected by filtration
  3. washwashed with water
  4. customto give the crude product

Sources & evidence

ORD record
ord-cd262e7391c5408d992a4a4c684770e9
Source dataset
uspto-grants-1994_04
Patent number
US05300282

Reaction notes

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