N-bromobutanimide → HCID 18993184, compound

HRID 375633Notes

Reaction equation

HRID 375633 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[S:14][C:13]([CH2:15][C:16]([OH:18])=[O:17])=[CH:12][CH:11]=1>Cl(O)(=O)(=O)=O>[Br:1][CH2:9][C:10]1[S:14][C:13]([CH2:15][C:16]([OH:18])=[O:17])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 45271772-(5-methylthiophen-2-yl)acetic Acid

Product 1

HCID 18993184HCID 18993184, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 24247Perchloric AcidCatalyst

Procedure

To a solution of N-bromosuccinimide (5.94 g, 33 mmol) in hexanes (16 mL) was added 5-methyl-2-carboxymethylthiophene (5.0 g, 32 mmol), prepared as in step 1, followed by 1 drop of perchloric acid. The reaction mixture was stirred for 22 hours at ambinet temperature and then partitioned between ethyl acetate and saturated aqueous HaHSO3 solution. The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo to give 6.17 g of 5-bromomethyl-2-carboxymethylthiophene as a yellow oil.

Workup

  1. custompartitioned between ethyl acetate and saturated aqueous HaHSO3 solution
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9a72a969e1c843cc89a85ea9a4cb1c47
Source dataset
uspto-grants-1996_01
Patent number
US05486525

Reaction notes

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