Methanesulfonyl chloride → Methyl 5-(chloromethyl)-2-methoxybenzoate

HRID 323407Notes

Reaction equation

HRID 323407 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([CH2:13]O)=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].C(N(CC)C(C)C)(C)C.CS([Cl:28])(=O)=O>ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([CH2:13][Cl:28])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 18465013Methyl 5-(hydroxymethyl)-2-methoxybenzoate

Product 1

HCID 240622Methyl 5-(chloromethyl)-2-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Combine methyl 2-methoxy-5-hydroxymethylbenzoate (1.34 g, 6.8 mmol) and N,N-diisopropylethylamine (1.4 mL) in dichloromethane (25 mL). Cool in a ice-bath. Add dropwise, methanesulfonyl chloride (0.56 mL). After 30 minutes, warm to ambient temperature. After 2 hours, dilute with dichloromethane and extract with 1 M hydrochloric acid solution and 5% sodium bicarbonate solution. Dry the organic layer over Na2SO4, filter, and concentrate in vacuo to give methyl 2-methoxy-5-chloromethylbenzoate: Rf=0.64 (silica gel, 1/1 ethyl acetate/hexane).

Workup

  1. temperatureCool in a ice-bath
  2. additionAdd dropwise
  3. waitAfter 2 hours
  4. extractionextract with 1 M hydrochloric acid solution and 5% sodium bicarbonate solution
  5. dry with materialDry the organic layer over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-b1fe6c8543724b74ac46d56b5eb48e09
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

Loading…