Sodium Hydroxide → Methyl 3-amino-5-bromo-1-benzothiophene-2-carboxylate

HRID 1685096Notes

Reaction equation

HRID 1685096 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[C:7]#[N:8].[SH:11][CH2:12][C:13]([O:15][CH3:16])=[O:14].[OH-].[Na+]>CN(C)C=O>[NH2:8][C:7]1[C:6]2[CH:9]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=2[S:11][C:12]=1[C:13]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 16907Methyl ThioglycolateHCID 27249005-Bromo-2-fluorobenzonitrile

Product 1

HCID 44542789Methyl 3-amino-5-bromo-1-benzothiophene-2-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-bromo-2-fluorobenzonitrile (13.5 g, 67.5 mmol) in N,N-dimethylformamide at 0° C. was added methyl 2-mercaptoacetate (6.45 mL, 70.88 mmol). The mixture was stirred at 0° C. for 30 minutes and 5N sodium hydroxide (20.25 mL) added. After stirring at 0° C. for 3 hours, the mixture was quenched with ice-water and the resulting precipitate collected by filtration and dried to give 18.5 g (96%) of a white solid. LCMS (APCI) m/z: 287(M+H)+.

Workup

  1. stirringAfter stirring at 0° C. for 3 hours
  2. customthe mixture was quenched with ice-water
  3. filtrationthe resulting precipitate collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-ecee2f9cba0e458990c4ec8ed601d4e0
Source dataset
uspto-grants-2012_04
Patent number
US08148384B2

Reaction notes

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