HCID 86717828, compound → HCID 70872838, compound

HRID 710494Notes

Reaction equation

HRID 710494 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7](N(OC)C)=[O:8])=[C:4]([Cl:13])[CH:3]=1.[CH3:14][Mg+].[Br-]>C1COCC1>[Br:1][C:2]1[S:6][C:5]([C:7](=[O:8])[CH3:14])=[C:4]([Cl:13])[CH:3]=1

Participants

4

Reactant 2

HCID 86717828HCID 86717828, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 70872838HCID 70872838, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-bromo-3-chloro-N-methoxy-N-methylthiophene-2-carboxamide (1 g, 3.5 mmol) in THF (10 mL) was added MeMgBr (1.1 mL, 3.5 mmol) under N2 at RT. The mixture was stirred at RT for 0.5 h and quenched by aqueous NH4Cl. The resulting solution was extracted with EtOAc. The organic layers were dried over Na2SO4, concentrated and purified by column to give 0.6 g of 1-(5-bromo-3-chlorothiophen-2-yl)ethanone. MS (M+H): 239, 241. 1H NMR (400 MHz, CDCl3): δ 6.95 (s, 1H), 2.57 (s, 3H).

Workup

  1. customquenched by aqueous NH4Cl
  2. extractionThe resulting solution was extracted with EtOAc
  3. dry with materialThe organic layers were dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by column

Sources & evidence

ORD record
ord-914b1486f930476c8da37ce6df4c1eb6
Source dataset
uspto-grants-2015_11
Patent number
US09181236B2

Reaction notes

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