N-bromobutanimide → Phenol, 3-(bromomethyl)-4-chloro-, 1-methanesulfonate

HRID 1861987Notes

Reaction equation

HRID 1861987 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][C:3]=1[CH3:13].[Br:14]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:12][S:9]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH2:13][Br:14])[CH:4]=1)(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 18621211HCID 18621211, compound

Product 1

HCID 18621194Phenol, 3-(bromomethyl)-4-chloro-, 1-methanesulfonate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of the product from step A (61.3 g, 301 mmol) in 500 ml of carbon tetrachloride was added N-bromosuccinimide (80.3 g, 451 mmol) and 2,2-azobisisobutyronitrile (7.40 g, 45.0 mmol). The reaction was stirred at 80° C. for 2.5 hr, concentrated in vacuo, and then suspended in 30% EtOAc/Hexane (300 mL). The solution was filtered and concentrated to give crude product. The crude product was purified by silica gel chromatography (20% EtOAc/Hexane) to provide the title product as a yellow oil

Workup

  1. concentrationconcentrated in vacuo
  2. filtrationThe solution was filtered
  3. concentrationconcentrated
  4. customto give crude product
  5. customThe crude product was purified by silica gel chromatography (20% EtOAc/Hexane)

Sources & evidence

ORD record
ord-25039430598a4c228f7a044ef707ed00
Source dataset
uspto-grants-2003_03
Patent number
US06534506B2

Reaction notes

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