Triethylamine → HCID 18536178, compound

HRID 2306226Notes

Reaction equation

HRID 2306226 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][S:18]([CH3:17])(=[O:20])=[O:19])=[CH:4][C:3]=1[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 728574-Bromo-m-cresol

Product 1

HCID 18536178HCID 18536178, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-bromo-3-methylphenol (9.87 g, 52.8 mmol) and triethylamine (10.70 g, 106 mmol) in CH2Cl2 (50 mL) at 0° C. was added methanesulfonyl chloride (7.25 g, 63.3 mmol), dropwise. After 30 min at 0° C., the reaction mixture was concentrated in vacuo. The residue was partitioned between saturated aqueous NaHCO3 and EtOAc. The layers were separated and the organic extract was washed with aqueous NaHCO3, then 3 N aqueous HCl, then brine, then dried over Na2SO4, filtered, and concentrated in vacuo to provide the titled product.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe residue was partitioned between saturated aqueous NaHCO3 and EtOAc
  3. customThe layers were separated
  4. extractionthe organic extract
  5. washwas washed with aqueous NaHCO3
  6. dry with material3 N aqueous HCl, then brine, then dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cc4a80c490a34e82b7d7f23b35427275
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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