Hydrochloric Acid → HCID 58123258, compound

HRID 1948682Notes

Reaction equation

HRID 1948682 reaction equation
C([Li])CCC.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH3:15])=[CH:9][CH:8]=1.Br[C:17]1[CH:18]=[CH:19][C:20]2[O:24][CH2:23][C:22](=O)[C:21]=2[CH:26]=1.Cl>O1CCCC1.O>[Br:6][C:7]1[CH:12]=[CH:11][C:10]2[O:13][CH:14]=[C:15]([C:17]3[CH:26]=[CH:21][C:20]([O:24][CH2:23][CH3:22])=[CH:19][CH:18]=3)[C:9]=2[CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 685234-BromophenetoleHCID 105127485-Bromobenzo[b]furan-3(2H)-oneHCID 178418339Butyllithium

Product 1

HCID 58123258HCID 58123258, compoundYield 45.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

4.95 ml (15% solution in n-hexane) of n-butyllithium are added to a solution, cooled to −78° C., of 1.03 ml (7.23 mmol) of 4-bromophenetole in 35 ml of tetrahydrofuran under nitrogen, and the mixture is stirred at −78° C. for one hour. A solution of 1.4 g (6.6 mmol) of 5-bromobenzofuran-3-one is subsequently added dropwise at such a rate that the temperature does not rise above −70° C., stirring is continued at −78° C. for one hour, the reaction mixture is then allowed to come to room temperature stirred at room temperature for a further 15 hours, finally 10 ml of 1N hydrochloric acid are added, and stirring is continued for a further one hour. After addition of 20 ml of water, the tetrahydrofuran is stripped off in vacuo, and the aqueous mixture remaining is extracted three times with 10 ml of diethyl ether each time. After the combined organic phases have been washed with 10 ml of saturated sodium chloride solution and after drying over sodium sulfate, the solvent is stripped off in a rotary evaporator, and the crude product is purified by column chromatography on silica gel (petroleum ether/ethyl acetate 98:2), giving 0.95 g of 5-bromo-3-(4-ethoxyphenyl)-benzofuran as colourless oil; LC/MS: 318 (M+H);

Workup

  1. customdoes not rise above −70° C.
  2. stirringstirring
  3. waitis continued at −78° C. for one hour
  4. customto come to room temperature
  5. stirringstirred at room temperature for a further 15 hours
  6. stirringstirring
  7. waitis continued for a further one hour
  8. extractionthe aqueous mixture remaining is extracted three times with 10 ml of diethyl ether each time
  9. washAfter the combined organic phases have been washed with 10 ml of saturated sodium chloride solution
  10. dry with materialafter drying over sodium sulfate
  11. customthe solvent is stripped off in a rotary evaporator
  12. customthe crude product is purified by column chromatography on silica gel (petroleum ether/ethyl acetate 98:2)

Sources & evidence

ORD record
ord-5251db3d72244706a42c9c58a645ac7b
Source dataset
uspto-grants-2013_03
Patent number
US08399509B2

Reaction notes

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