4-Bromothioanisole → HCID 18400181, compound

HRID 1078660Notes

Reaction equation

HRID 1078660 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[CH:4][CH:3]=1.[Li]C(C)(C)C.[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:23](=[O:27])[CH2:24][CH2:25][CH:26]=2)=[CH:18][CH:17]=1>CCOCC>[CH3:9][S:8][C:5]1[CH:6]=[CH:7][C:2]([C:23]2([OH:27])[CH2:24][CH2:25][CH:26]=[C:22]2[C:19]2[CH:20]=[CH:21][C:16]([F:15])=[CH:17][CH:18]=2)=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 660374-BromothioanisoleHCID 11469378HCID 11469378, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 18400181HCID 18400181, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 3.86 g (19 mmol) of 4-bromothioanisole in 90 mL of Et2O cooled at -78° C., was added 22 mL of 1.7 M solution of t-BuLi in penlane (38 mmol) dropwise. The reaction mixture was stirred for 15 min at -78° C. and a solution of 2.23 g of 2-(4-Fluorophenyl)-2-cyclopenten-1-one in 10 mL of Et2O was added. After stirring for 15 min at -78° C., the reaction mixture was warmed to 0° C., and quenched with 50 mL of sat. NH4Cl. The product was extracted with 100 mL EtOAc, dried over Na2SO4, and purified by flash chromatography, eluted with 4:1 hexane/EtOAc to give 3.4 g of the desired product.

Workup

  1. stirringAfter stirring for 15 min at -78° C.
  2. temperaturethe reaction mixture was warmed to 0° C.
  3. customquenched with 50 mL of sat. NH4Cl
  4. extractionThe product was extracted with 100 mL EtOAc
  5. dry with materialdried over Na2SO4
  6. custompurified by flash chromatography
  7. washeluted with 4:1 hexane/EtOAc

Sources & evidence

ORD record
ord-0d0f65f5cc9b45abae95957961b49b75
Source dataset
uspto-grants-1996_08
Patent number
US05550142

Reaction notes

Loading…