Potassium Carbonate → HCID 58764046, compound

HRID 2387074Notes

Reaction equation

HRID 2387074 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH2:9][CH3:10])[CH:3]=1.Br[C:12]1[S:13][CH:14]=[CH:15][N:16]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)=[C:4]([CH2:9][CH3:10])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 764302-BromothiazoleHCID 878774-Bromo-2-ethylphenol

Product 1

HCID 58764046HCID 58764046, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 4-bromo-2-ethyl-phenol (1.00 g, 4.97 mmol) in DMF (40 mL) was added 2-bromothiazole (0.341 mL, 3.82 mmol) and finely crushed K2CO3 (3.17 g, 22.9 mmol). The mixture was stirred at 150° C. for 15 hours, at which time the hot solution was filtered through filter paper. The filtrate was diluted with CH2Cl2 and H2O and then brought to pH 6.0 with 6.0N HCl. The aqueous layer was extracted with CH2Cl2 and the organic layer was washed with H2O and brine. The organic layer was dried over Na2SO4 and concentrated to yield a yellow oil (1.0 g, 92%). 1H NMR (300 MHz, CDCl3): δ 1.19 (t, J=7.6 Hz, 3 H), 2.62 (q, J=7.5 Hz, 2 H), 6.79 (d, J=3.8 Hz, 1 H), 7.10 (d, J=8.5 Hz, 1 H), 7.19 (d, J=3.8 Hz, 1 H), 7.35 (dd, J=8.7, 2.4 Hz, 1 H), 7.43 (d, J=2.4 Hz, 1 H).

Workup

  1. filtrationwas filtered
  2. filtrationthrough filter paper
  3. additionThe filtrate was diluted with CH2Cl2 and H2O
  4. extractionThe aqueous layer was extracted with CH2Cl2
  5. washthe organic layer was washed with H2O and brine
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8047c8358bad4a2dbf1371fe316cf000
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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