Potassium Carbonate → 2-(4-(5-Bromo-2-chlorobenzyl)phenyl)ethanol

HRID 2038491Notes

Reaction equation

HRID 2038491 reaction equation
C([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]2[CH:19]=[C:18]([Br:20])[CH:17]=[CH:16][C:15]=2[Cl:21])=[CH:9][CH:8]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.O>[Br:20][C:18]1[CH:17]=[CH:16][C:15]([Cl:21])=[C:14]([CH:19]=1)[CH2:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][OH:4])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 595577874-(5-Bromo-2-chlorobenzyl)phenethyl acetate

Product 1

HCID 595577662-(4-(5-Bromo-2-chlorobenzyl)phenyl)ethanolYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

4-(5-bromo-2-chlorobenzyl)phenethyl acetate (intermediate BG) (400 mg, 1.09 mmol) and potassium carbonate (481 mg, 3.48 mmol) were stirred at room temperature in a mixture of 3 mL methyl alcohol and 0.5 mL water for 3 h. Solvents were evaporated and the residue taken up in 25 mL ether was washed with water (5 mL) and brine (20 mL), dried (Na2SO4), filtered and evaporated. Purification on silica gel using an ISCO column with 15:1 hexane:EtOAc gave intermediate BH (271 mg, yield 76%). 1H NMR (300 MHz, CDCl3): δ 7.27-7.07 (m, 7H), 4.02 (s, 2H), 3.84 (m, 2H), 2.86 (m, 3H); LC-ESI-MS (m/z): 325 (M+H).

Workup

  1. customSolvents were evaporated
  2. washwas washed with water (5 mL) and brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification on silica gel using an ISCO column with 15:1 hexane
  7. customEtOAc gave intermediate BH (271 mg, yield 76%)

Sources & evidence

ORD record
ord-a40de456bf65496d83dc5b12c6907868
Source dataset
uspto-grants-2013_11
Patent number
US08575321B2

Reaction notes

Loading…