4-Toluenesulfonyl chloride → HCID 86669924, compound

HRID 1506479Notes

Reaction equation

HRID 1506479 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[N:12][OH:13])[CH2:7][CH2:6][CH2:5]2.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>N1C=CC=CC=1>[S:20]([O:13][N:12]=[C:8]1[C:9]2[C:4](=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=2)[CH2:5][CH2:6][CH2:7]1)([C:17]1[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=1)(=[O:22])=[O:21]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 859418886-Bromo-3,4-dihydro-1(2H)-naphthalenone oxime

Product 1

HCID 86669924HCID 86669924, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 6-bromo-3,4-dihydronaphthalen-1(2H)-one oxime (2.5 g, 10.41 mmol) in pyridine (5 mL) was added p-toluenesulfonyl chloride (2.184 g, 11.45 mmol) in one lot at room temperature. The reaction mixture was stirred at room temperature for 20 h. Ice cubes (˜10 g) were added to the flask and the contents stirred at room temperature for 30 min. The solid that separated out was filtered and washed with water (3×20 mL), dried over sodium sulfate and concentrated to yield 6-bromo-3,4-dihydronaphthalen-1(2H)-one O-tosyl oxime (3.92 g, 9.94 mmol, 95% yield) as light pink solid. The solid was azeotroped once with toluene (10 mL) and used for the subsequent reaction. MS M+1=395.

Workup

  1. additionIce cubes (˜10 g) were added to the flask
  2. stirringthe contents stirred at room temperature for 30 min
  3. customThe solid that separated out
  4. filtrationwas filtered
  5. washwashed with water (3×20 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6d914bcc434e48b5bace48ae5b64b305
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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