Triethylamine → 2-Methoxyphenethyl bromide

HRID 1870973Notes

Reaction equation

HRID 1870973 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

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 NaHCO3 (2×), water and dried with MgSO4. Upon removal of solvents, the residue was dissolved in 50 ml of acetone and to the solution was added LiBr (11.34 g, 130.6 mmol). 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 NaHCO3 (2×), water
  2. dry with materialdried with MgSO4
  3. customUpon removal of solvents
  4. dissolutionthe residue was dissolved in 50 ml of acetone and to the solution
  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-57cf58c48104486e96600c709ed483fa
Source dataset
uspto-grants-2000_08
Patent number
US06100293

Reaction notes

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