4-Toluenesulfonyl chloride → HCID 22917423, compound

HRID 37533Notes

Reaction equation

HRID 37533 reaction equation
[Br:1][C:2]1[CH2:6][C:5]([CH2:9]O)([CH2:7]O)[CH2:4][C:3]=1[Br:11].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1>N1C=CC=CC=1>[Br:1][C:2]1[CH2:6][C:5]([CH2:9][S:18]([C:15]2[CH:16]=[CH:17][C:12]([CH3:22])=[CH:13][CH:14]=2)(=[O:20])=[O:19])([CH2:7][S:18]([C:15]2[CH:16]=[CH:17][C:12]([CH3:22])=[CH:13][CH:14]=2)(=[O:20])=[O:19])[CH2:4][C:3]=1[Br:11]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 13866078HCID 13866078, compound

Product 1

HCID 22917423HCID 22917423, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Under nitrogen, a stirred solution of 5.7 g (19.9 mmol) of 1,2-dibromo-4,4-di(hydroxymethyl)cyclopentene (Step 5) in 50 mL of pyridine at ambient temperature was treated with 19 g (99.7 mmol) of p-toluenesulfonyl chloride. The reaction was allowed to stir overnight and was concentrated in vacuo. The residue was dissolved ethyl acetate and washed twice with 3% hydrochloric acid followed by brine. The solution was dried (Na2SO4) and concentrated in vacuo to give 5.2 g (44%) of 1,2-dibromo-4,4-di(tosylmethyl)cyclopentene (14 in Synthetic Scheme V) as a colorless semisolid: NMR (CDCl3) d 2.42 (s, 4H), 2.47 (s, 6H), 3.90 (s, 4H), 7.37 (d, J=8 Hz, 4H), 7.74 (d, J=8 Hz, 4H).

Workup

  1. concentrationwas concentrated in vacuo
  2. dissolutionThe residue was dissolved ethyl acetate
  3. washwashed twice with 3% hydrochloric acid
  4. dry with materialThe solution was dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1e064208762b423387df82f3aa20b085
Source dataset
uspto-grants-1995_05
Patent number
US05420287

Reaction notes

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