N-bromobutanimide → HCID 9993958, compound

HRID 247856Notes

Reaction equation

HRID 247856 reaction equation
[CH2:1]([CH:5]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:6]([OH:8])=[O:7])[CH2:2][C:3]#[CH:4].[Br:16]N1C(=O)CCC1=O.C(=O)(O)[O-].[K+].[OH-].C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl>[Br:16]/[CH:4]=[C:3]1\[CH2:2][CH2:1][CH:5]([O:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:6](=[O:8])[O:7]\1

Participants

6

Reactant 4

HCID 67184N-bromobutanimideHCID 516893Potassium BicarbonateHCID 2723671Tetrabutylammonium HydroxideHCID 10375629HCID 10375629, compound

Product 1

HCID 9993958HCID 9993958, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of the α-(3-butynyl)phenoxyacetic acid of Part A, (74 mg, 0.36 mmol), N-bromosuccinimide (132 mg, 0.720 mmol), potassium bicarbonate (98 mg, 0.90 mmol) and 0.4M aqueous tetrabutylammonium hydroxide (0.11 mL, 0.044 mmol) in CH2Cl2 (8 mL) was stirred at room temperature in the dark for 7 h. The mixture was washed with 5% Na2S2O3 and saturated NaCl. The organic Iayer was dried (MgSO4) and the solvent was removed in vacuo to give 42 mg of an oil.

Workup

  1. washThe mixture was washed with 5% Na2S2O3 and saturated NaCl
  2. dry with materialThe organic Iayer was dried (MgSO4)
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-7f510968812d445a8e68ab5c3c514727
Source dataset
uspto-grants-1993_05
Patent number
US05208244

Reaction notes

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