Triethylamine → 2-Methoxyphenethyl bromide

HRID 2287475Notes

Reaction equation

HRID 2287475 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[CH2:5][CH2:6]O.CN(C1C=CC=CN=1)C.CCN(CC)CC.CS(Cl)(=O)=O.[Li+].[Br-:34]>C(Cl)Cl.CCOCC.CCCCCC>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[CH2:5][CH2:6][Br:34]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 31297Methanesulfonyl chlorideHCID 819092-Methoxyphenethyl alcoholHCID 82050Lithium Bromide

Product 1

HCID 5781992-Methoxyphenethyl bromide

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To a solution of 2-methoxyphenethyl alcohol (5.0 g, 32.6 mmol) in 40 ml of CH2Cl2 was added dimethylaminopyridine (DMAP) (10 mg), Et3N (11.4 ml, 81.8 mmol) and MsCl (5.05 ml, 65.2 mmol) at 0° C. After 1 h, the reaction mixture was poured into hexane and it was washed with aqueous NaHCO3 (2×), water and dried with MgSO4. Upon removal of the solvents, the residue was dissolved in 50 ml of acetone and LiBr (11.34 g, 130.6 mmol) was added. After the solution was heated at reflux for 16 h, it was poured into ether and washed with water, dried with MgSO4, filtered and dried to afford 2-methoxyphenethyl bromide.

Workup

  1. washwas washed with aqueous NaHCO3 (2×), water
  2. dry with materialdried with MgSO4
  3. customUpon removal of the solvents
  4. dissolutionthe residue was dissolved in 50 ml of acetone
  5. temperatureAfter the solution was heated
  6. temperatureat reflux for 16 h
  7. washwashed with water
  8. dry with materialdried with MgSO4
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-c234ea0255be4a1d925e147d66090a11
Source dataset
uspto-grants-2000_07
Patent number
US06083980

Reaction notes

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