Triethylamine → (1,1'-Biphenyl)-4-sulphonyl chloride

HRID 1249755Notes

Reaction equation

HRID 1249755 reaction equation
[S:1]([Cl:5])(Cl)(=[O:3])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:25]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:30]=[CH:29][C:28](S(O)(=O)=O)=[CH:27][CH:26]=1.C(N(CC)CC)C>C(Cl)Cl>[C:25]1([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:30]=[CH:29][C:28]([S:1]([Cl:5])(=[O:3])=[O:2])=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 16673(1,1'-Biphenyl)-4-sulfonic acidHCID 24648Sulfuryl chloride

Product 1

HCID 74192(1,1'-Biphenyl)-4-sulphonyl chlorideYield 45.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Sulfuryl chloride (392 μl, 4.74 mmol) was added dropwise to a 0° C. suspension of triphenylphosphine-resin (1.58 g) in methylene chloride (10 ml). A solution of 4-biphenylsulfonic acid (400 mg, 1.58 mmol) and triethylamine (220 μl) in methylene chloride (5 ml) was added. The mixture was stirred at room temperature for 6 hours and stored at 5° C. for 3 days. This was filtered and the filtrate was evaporated. The residue was coevaporated with toluene twice to give the crude product as a white solid. Purification of the crude product by chromatography (silica, methylene chloride) gave 180 mg of the title product as a white solid.

Workup

  1. waitstored at 5° C. for 3 days
  2. filtrationThis was filtered
  3. customthe filtrate was evaporated
  4. customto give the crude product as a white solid
  5. customPurification of the crude product by chromatography (silica, methylene chloride)

Sources & evidence

ORD record
ord-0c2e1401a70c4bb1a1e714e32617cec8
Source dataset
uspto-grants-2002_01
Patent number
US06335324B1

Reaction notes

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