Hydrochloric Acid → 4-Bromobenzylsulfonyl chloride

HRID 1049000Notes

Reaction equation

HRID 1049000 reaction equation
ClN1C(=[O:7])CCC1=O.[Br:9][C:10]1[CH:20]=[CH:19][C:13]([CH2:14][S:15]C(=O)C)=[CH:12][CH:11]=1.[OH2:21].[ClH:22]>C(#N)C>[Br:9][C:10]1[CH:20]=[CH:19][C:13]([CH2:14][S:15]([Cl:22])(=[O:7])=[O:21])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 31398ChlorosuccinimideHCID 5107661S-[(4-Bromophenyl)methyl] ethanethioate

Product 1

HCID 5987644-Bromobenzylsulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
15 °C

Procedure

To a solution of N-chlorosuccinimide (3.95 g, 29.6 mmol) in acetonitrile (11.6 mL) and 1 M HCl (2.31 mL) at 0° C. was slowly added a solution of thioacetic acid S-(4-bromo-benzyl)ester (1.81 g, 7.39 mmol) in acetonitrile (6.3 mL) over 60 minutes whilst allowing the reaction to warm to 15° C. The remaining solution was added and reaction left to warm to room temperature for 10 minutes. The mixture was cooled to 0° C. and stirred for 1 hour. Water was added and the product was extracted with EtOAc, washed with brine, dried with Na2SO4, concentrated to give (4-bromo-phenyl)-methanesulfonyl chloride (2.6 g, 9.6 mmol). 1H NMR (300 MHz, CDCl3): δ 7.60 (d, 2H), 7.36 (d, 2H), 4.81 (s, 2H).

Workup

  1. customthe reaction
  2. additionThe remaining solution was added
  3. customreaction
  4. waitleft
  5. temperatureto warm to room temperature for 10 minutes
  6. temperatureThe mixture was cooled to 0° C.
  7. extractionthe product was extracted with EtOAc
  8. washwashed with brine
  9. dry with materialdried with Na2SO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-bf416d48576344fc8d608fe552266782
Source dataset
uspto-grants-2016_07
Patent number
US09382222B2

Reaction notes

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