Oxalyl chloride → (2-Benzyloxy-phenyl)-methanesulfonyl chloride

HRID 2061727Notes

Reaction equation

HRID 2061727 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][S:16]([OH:19])(=O)=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:23])=O>CN(C)C=O.O1CCCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][S:16]([Cl:23])(=[O:19])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 86065129(2-Benzyloxy-phenyl) methanesulfonic acid

Product 1

HCID 11347020(2-Benzyloxy-phenyl)-methanesulfonyl chlorideYield 77.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Tetrahydrofuran (10 ml), (2-Benzyloxy-phenyl)-methanesulfonic acid (138 mg), and N,N-dimethylformamide (2 drops) was cooled to −78° C. and oxalyl chloride (315 mg) was added slowly. The reaction mixture was stirred for 3 h from −78° C. to 0° C. The reaction mixture was clarified by filtration. The filtrate was washed with iced-water and heptane, and dried to give (2-benzyloxy-phenyl)-methanesulfonyl chloride (114 mg, 77%). 1H NMR (400 MHz, CDCl3): δ 5.06 (s, 2 H) 5.15 (s, 2 H) 7.04 (m, 2 H) 7.42 (m, 7 H).

Workup

  1. filtrationThe reaction mixture was clarified by filtration
  2. washThe filtrate was washed with iced-water and heptane
  3. customdried

Sources & evidence

ORD record
ord-fee414f89c674e65a0966754a0d1d1d2
Source dataset
uspto-grants-2012_10
Patent number
US08283373B2

Reaction notes

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