4-Toluenesulfonyl chloride → 4-Bromo-2-methoxyphenyl 4-methylbenzene-1-sulfonate

HRID 2384878Notes

Reaction equation

HRID 2384878 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([O:9][CH3:10])[CH:3]=1.[S:11](Cl)([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12].CCN(CC)CC>C(Cl)Cl.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][S:11]([C:14]2[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[C:4]([O:9][CH3:10])[CH:3]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 2622344-Bromo-2-methoxyphenol

Product 1

HCID 866292054-Bromo-2-methoxyphenyl 4-methylbenzene-1-sulfonateYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 4-bromo-2-methoxy-phenol (1.032 g, 5.08 mmol) in CH2Cl2 (10 mL), and treat with TsCl (0.969 g, 5.08 mmol) followed by Et3N (1.06 mL, 7.62 mmol). Stir the reaction at RT for 2 h. Dilute with EtOAc (100 mL) and wash with water (2×30 mL). Dry with Na2SO4, filter, and concentrate to give 1.81 g (100%) of the title compound. MS/ES m/z (81Br) 380.9 [M+Na]+.

Workup

  1. customthe reaction at RT for 2 h
  2. washwash with water (2×30 mL)
  3. dry with materialDry with Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-aae7e07e99a94120a1b7e969037e6908
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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