Diethyl Ether → HCID 89480007, compound

HRID 589234Notes

Reaction equation

HRID 589234 reaction equation
[Br:1]N1C(=O)CCC1=O.[Br:9][C:10]1[CH:14]=[CH:13][S:12][C:11]=1[C:15]1[S:16][C:17]([CH3:20])=[CH:18][CH:19]=1.C(OC(=O)C)(=O)C.CCOCC>C(O)(=O)C.O>[Br:9][C:10]1[CH:14]=[C:13]([Br:1])[S:12][C:11]=1[C:15]1[S:16][C:17]([CH3:20])=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 67184N-bromobutanimideHCID 89480001HCID 89480001, compound

Product 1

HCID 89480007HCID 89480007, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

N-Bromosuccinimide (15.55 g, 87 mmol) was added portionwise to stirred solution of 3-bromo-5′-methyl-2,2′-bithiophene (20.56 g, 79 mmol) in glacial acetic acid (200 mL) containing acetic anhydride (25 mL) at RT. The mixture was stirred and monitored by TLC. After completion (1.5 h) the reaction was diluted with water (200 mL) and the oily phase was taken into ether and separated. The aqueous phase was extracted with ether. The combined organic phases were washed with 1 M NaOH solution followed by water. Removal of the solvent left a solidifying oil, which was sonicated in methanol yielding after filtration and drying 3,5-dibromo-5′-methyl-2,2′-bithiophene as off-white solid (single spot on TLC). Yield: 20.6 g (77%). 1H NMR (600 MHz, CD2Cl2) ppm 7.13 (d, J=3.6 Hz, 1H), 6.97 (s, 1H), 6.74-6.72 (m, 1H), 2.48-2.47 (m, 3H)

Workup

  1. customseparated
  2. extractionThe aqueous phase was extracted with ether
  3. washThe combined organic phases were washed with 1 M NaOH solution
  4. customRemoval of the solvent
  5. waitleft a solidifying oil, which
  6. customwas sonicated in methanol yielding
  7. filtrationafter filtration
  8. dry with materialdrying 3,5-dibromo-5′-methyl-2,2′-bithiophene as off-white solid (single spot on TLC)

Sources & evidence

ORD record
ord-8f370e0e6a0e4f7d9acb16b5e3e2445a
Source dataset
uspto-grants-2016_01
Patent number
US09227986B2

Reaction notes

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