Triethylamine → HCID 86631769, compound

HRID 1715859Notes

Reaction equation

HRID 1715859 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[CH2:5][OH:6].CCN(CC)CC.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[CH2:5][O:6][S:20]([CH3:19])(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 12909342(3-Chloro-5-methoxyphenyl)methanol

Product 1

HCID 86631769HCID 86631769, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-chloro-5-methoxybenzyl alcohol (14.7 mmol, 2.54 g) in DCM (20 ml) was added Et3N (22 mmol, 2.23 g, 3.1 ml) and the solution was cooled to −10° C. on an acetone-ice batch. Methanesulfonic chloride (17.7 mmol, 2.03 g, 1.4 ml) was added dropwise under stirring. After 45 min the mixture was separated between DCM and H3PO4 (5% v/v in water, cold). The organic phase was washed with H3PO4 (5% v/v in water, cold), NaHCO3 (10% in water, cold), brine and dried (MgSO4). Filtration and removal of solvents under reduced pressure yielded the title compound (3.43 g, 93%) as a white solid. The product was used in the next step without further purification. 1H NMR (CDCl3, 500 MHz) δ 2.97 (s, 3H), 3.82 (s, 3H), 5.16 (s, 2H), 6.82 (s, 1H), 6.90 (s, 1H) and 6.98 (s, 1H).

Workup

  1. customAfter 45 min the mixture was separated between DCM and H3PO4 (5% v/v in water, cold)
  2. washThe organic phase was washed with H3PO4 (5% v/v in water, cold), NaHCO3 (10% in water, cold), brine
  3. dry with materialdried (MgSO4)
  4. filtrationFiltration and removal of solvents under reduced pressure

Sources & evidence

ORD record
ord-29a358f7cb9c4fd1bfe7426b9f38f500
Source dataset
uspto-grants-2010_09
Patent number
US07799947B2

Reaction notes

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