Sodium Acetate → 3-(5-Bromothiophen-2-yl)-3-oxopropyl acetate

HRID 1484971Notes

Reaction equation

HRID 1484971 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7](=[O:11])[CH2:8][CH2:9]Cl)=[CH:4][CH:3]=1.[CH3:12][C:13]([O-:15])=[O:14].[Na+]>C(O)(=O)C>[C:13]([O:15][CH2:9][CH2:8][C:7]([C:5]1[S:6][C:2]([Br:1])=[CH:3][CH:4]=1)=[O:11])(=[O:14])[CH3:12]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 128676641-(5-Bromothiophen-2-yl)-3-chloropropan-1-one

Product 1

HCID 581694203-(5-Bromothiophen-2-yl)-3-oxopropyl acetateYield 541.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

To the mixture of 1-(5-bromothiophen-2-yl)-3-chloropropan-1-one (2.8 g, 1.6 mmol, 1.0 eq), NaOAc (4.5 g, 55.3 mmol, 5 eq) and KI (200 mg) in acetic acid (16 mL) was stirred at 130° C. for overnight. The mixture was extracted with CH2Cl2 (3×40 ml). The combined organic layers were washed (brine), dried (Na2SO4), filtered and concentrated to give yellow oil 3-(5-bromothiophen-2-yl)-3-oxopropyl acetate (2.4 g, 76.2%). LC-MS (m/z)=278.1 [M+H]+

Workup

  1. extractionThe mixture was extracted with CH2Cl2 (3×40 ml)
  2. washThe combined organic layers were washed (brine)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-084a0d1d274749099e563b97ab63ee30
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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