Sulfuryl chloride → 2-(Benzyloxy)benzene-1-sulfonyl chloride

HRID 1814278Notes

Reaction equation

HRID 1814278 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.S(=O)=O.C1COCC1.[S:29](Cl)([Cl:32])(=[O:31])=[O:30]>C(OCC)C.C1COCC1.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:29]([Cl:32])(=[O:31])=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 24648Sulfuryl chlorideHCID 5618281-(Benzyloxy)-2-bromobenzeneHCID 70133875sulfur dioxide THFHCID 178418339Butyllithium

Product 1

HCID 219624592-(Benzyloxy)benzene-1-sulfonyl chlorideYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21868444Ether tetrahydrofuranSolvent

Procedure

To 2-benzyloxy-1-bromo benzene (4.0 g, 15.2 mmol) in diethyl ether/THF (1:1, 100 mL) at −78° C. was added n-butyllithium (2 equiv.). After 30 min sulfur dioxide/THF (1:1, 40 mL) was added. The reaction warmed to room temperature over 1.5 h and the solvent was removed under reduced pressure. Hexanes (75 mL) was added and the reaction was cooled to 0° C. prior to adding sulfuryl chloride (2 equiv.). After 15 min the reaction was poured into water, washed with brine and dried over magnesium sulfate to give a colorless oil. Chromatography silica gel, eluting with 1:1 hexanes/diethyl ether gave 2-benzyloxy-benzenesulfonyl chloride (3.11 g, 72%) as a colorless solid. 1H NMR (CDCl3) 8.00(d,1H), 7.65(t,1H), 7.54(d,2H), 7.38(m,3H), 7.12(m,2H), 5.37 (s,2H).

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionHexanes (75 mL) was added
  3. temperaturethe reaction was cooled to 0° C.
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. customto give a colorless oil
  7. washChromatography silica gel, eluting with 1:1 hexanes/diethyl ether

Sources & evidence

ORD record
ord-37289939d56143b29f62ade692478c15
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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