4-Nitrophenethyl bromide → HCID 10944126, compound

HRID 1190123Notes

Reaction equation

HRID 1190123 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.[C:13]([O-:16])(=[S:15])[CH3:14].[K+]>CS(C)=O.CCOC(C)=O>[N+:10]([C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][S:15][C:13](=[O:16])[CH3:14])=[CH:5][CH:6]=1)([O-:12])=[O:11]

Participants

5

Reactant 2

HCID 792664-Nitrophenethyl bromideHCID 23670855Potassium ethanethioate

Product 1

HCID 10944126HCID 10944126, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2.00 g (8.69 mmol) of 1-(2-bromo-ethyl)-4-nitro-benzene in DMSO (10 mL) was treated with 1.99 g (17.4 mmol) of potassium thioacetate and stirred at RT for 5 h. The mixture was diluted with EtOAc (100 mL) and washed with water (6×60 mL). The organic layer was dried (MgSO4) and concentrated in vacuo to afford 1.48 g (76%) of the title compound as a brown oil: 1H-NMR (CD3OD; 400 MHz): δ 8.23-8.15 (m, 2H), 7.60-7.53 (m, 2H), 3.27-3.10 (m, 4H), 3.03-2.94 (m, 3H).

Workup

  1. washwashed with water (6×60 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4f022b05dea9441e9494160398e19bd6
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

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