Benzyl Bromide → HCID 90070487, compound

HRID 590522Notes

Reaction equation

HRID 590522 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6](=[O:10])[CH2:7][CH2:8][CH2:9][C:2]1=2.[Li+].CC([N-]C(C)C)C.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Cl-].[NH4+]>C1COCC1>[CH2:19]([CH:7]1[CH2:8][CH2:9][C:2]2[S:1][CH:5]=[CH:4][C:3]=2[C:6]1=[O:10])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 25517Ammonium ChlorideHCID 834184,5,6,7-Tetrahydro-4-oxothionaphtheneHCID 2724682Lithium diisopropylamide

Product 1

HCID 90070487HCID 90070487, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

6,7-Dihydrobenzo[b]thiophen-4(5H)-one (0.5 g, 3.3 mmol) in THF (7.5 mL) was added drop-wise to LDA (2.2 mL, 3.67 mmol) under a nitrogen atmosphere at −78° C. The mixture was warmed to −30° C. for 10 min before being re-cooled to −78° C. Benzyl bromide (1.17 mL, 9.9 mmol) was then added drop-wise and the mixture was gradually warmed to room temperature and stirred for 18 hr. Saturated ammonium chloride solution was added to the reaction mixture and product was extracted into ethyl acetate (×3). The combined organic extracts were combined, dried (MgSO4) and concentrated in vacuo. The crude residue was purified on silica gel using a gradient elution of 0-50% ethyl acetate in iso-hexane to afford the title compound as a yellow oil (0.55 g, 62%).

Workup

  1. temperaturebefore being re-cooled to −78° C
  2. temperaturethe mixture was gradually warmed to room temperature
  3. extractionwas extracted into ethyl acetate (×3)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified on silica gel using
  7. washa gradient elution of 0-50% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-16c3c9e8164a4a4bb363d0b766070ccd
Source dataset
uspto-grants-2016_01
Patent number
US09233982B2

Reaction notes

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