Pyridine → Benzoic acid, 4-[(methylsulfonyl)oxy]-, methyl ester

HRID 709463Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.N1C=CC=CC=1.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C1COCC1>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([O:10][S:19]([CH3:18])(=[O:21])=[O:20])=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4-Hydroxy-benzoic acid methyl ester (3.19 g, 21 mmol) was dissolved together with pyridine (1.97 g, 25 mmol) in dry THF (20 mL) and after cooling down to 0° C., methanesulfonyl chloride (2.29 g, 20 mmol) was added dropwise. The ice bath was removed and mixture was stirred at r.t. for 5 h. After diluting with DCM and extraction with water and aq. HCl (2N), the organic layer was dried (MgSO4) and evaporated to afford the crude but highly pure product as a solid which was used in the next step without further purification (4.38 g, 95.1%). 1H NMR (400 MHz, CDCl3): δ 8.07-8.09 (d, 2H), 7.32-7.34 (d, 2H), 3.90 (s, 3H), 3.16 (s, 3H).

Workup

customThe ice bath was removed
additionAfter diluting with DCM and extraction with water and aq. HCl (2N)
dry with materialthe organic layer was dried (MgSO4)
customevaporated
customto afford the crude but highly pure product as a solid which
customwas used in the next step without further purification (4.38 g, 95.1%)

Sources & evidence

ORD record: ord-7ed561784c2f4d99b6011ffce2183adf
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181181B2

Reaction notes

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