Bromine → HCID 57701125, compound

HRID 332570Notes

Reaction equation

HRID 332570 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[Br:21]Br.OS([O-])=O.[Na+]>C(O)(=O)C>[Br:21][C:20]1[CH:19]=[C:6]([CH:5]=[CH:4][C:3]=1[O:2][CH3:1])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH3:18])(=[O:16])=[O:17])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 23665763Sodium BisulfiteHCID 57701123HCID 57701123, compound

Product 1

HCID 57701125HCID 57701125, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A round bottom was charged with N-[4-(4-Methoxy-benzyl)-phenyl]-methane sulfonamide (8) (1.4 g, 4.8 mmol), acetic acid (15 mL) and slow addition of bromine (5 minute period, 0.23 mL, 5.2 mmol). The reaction mixture was stirred at room temperature overnight. To the yellow homogeneous reaction mixture 15% w/v of aq. NaHSO3 (50 mL) was added. The reaction mixture formed a white precipitate. The reaction mixture was stirred for 30 minutes. Then the solid was collected, rinsed several times with water and dried in vacuo to provide 961.9 mg (56% yield) of product (9).

Workup

  1. additionwas added
  2. customThe reaction mixture formed a white precipitate
  3. stirringThe reaction mixture was stirred for 30 minutes
  4. customThen the solid was collected
  5. washrinsed several times with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-c6bb9a06b3f541d0867ea171cf6d3c3e
Source dataset
uspto-grants-2014_11
Patent number
US08877816B2

Reaction notes

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