Phosphorus pentachloride → 4-(1,1-Dimethylethyl)-2-methoxybenzenesulfonyl chloride

HRID 1925690Notes

Reaction equation

HRID 1925690 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11](O)(=[O:13])=[O:12])=[C:7]([O:15][CH3:16])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)(Cl)(Cl)[Cl:18]>ClC(Cl)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([Cl:18])(=[O:13])=[O:12])=[C:7]([O:15][CH3:16])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 59180418HCID 59180418, compound

Product 1

HCID 591803954-(1,1-Dimethylethyl)-2-methoxybenzenesulfonyl chlorideYield 65.5%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To cooled (0° C.) solution of 30 (12.0 g; 49.12 mmol) in dichloroethane (200 mL) was added phosphorus pentachloride (20.5 g; 98.24 mmol) slowly and portion-wise. After addition was complete, the reaction was heated at reflux overnight, cooled to room temperature, and then concentrated under reduced pressure. The resulting crude residue was purified by automated silica gel column chromatography (Biotage®) eluting with ethyl acetate/hexanes (0 to 50% v/v over 400 mL gradient elution) to give the title product as a dark solid (8.45 g; 65% yield).

Workup

  1. additionAfter addition
  2. temperaturethe reaction was heated
  3. temperatureat reflux overnight
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting crude residue was purified by automated silica gel column chromatography (Biotage®)
  6. washeluting with ethyl acetate/hexanes (0 to 50% v/v over 400 mL gradient elution)

Sources & evidence

ORD record
ord-dcf1e3462ffd4e80a5c3af3bbe618f59
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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