Dimethylformamide → HCID 59761338, compound

HRID 1754949Notes

Reaction equation

HRID 1754949 reaction equation
CN(C)C=O.S(Cl)([Cl:8])=O.[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][CH2:18][S:19]([O-:22])(=O)=[O:20].[Na+]>C1(C)C=CC=CC=1>[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][CH2:18][S:19]([Cl:8])(=[O:22])=[O:20]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 59761283HCID 59761283, compound

Product 1

HCID 59761338HCID 59761338, compoundYield 104%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

N,N-Dimethylformamide (4.2 mL) and thionyl chloride (5.1 mL, 69.7 mmol) were sequentially added to a suspension of sodium 2-(2-bromo-phenyl)ethanesulfonate (4.00 g, 13.9 mmol) in toluene. The mixture was stirred at 100° C. for 66 hours and then poured into ice water. The organic layer and the aqueous layer were separated, and the aqueous layer was extracted with ether. The organic layers were combined and sequentially washed with water and saturated brine, and then dried over sodium sulfate and concentrated under reduced pressure to give 2-(2-bromophenyl)ethanesulfonyl chloride (4.10 g). This was used in the next step without further purification.

Workup

  1. customThe organic layer and the aqueous layer were separated
  2. extractionthe aqueous layer was extracted with ether
  3. washsequentially washed with water and saturated brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-10960594a8ab4eec987022fdd5f28961
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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