Ethyl Acetate → HCID 18518168, compound

HRID 1843942Notes

Reaction equation

HRID 1843942 reaction equation
[C-:1]#[N:2].[Na+].Br[CH2:5][C:6]1[C:7]2[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:8]=2[S:9][CH:10]=1.C(OC(=O)C)C>O.CN(C=O)C.CCCCCC>[F:15][C:13]1[CH:12]=[CH:11][C:8]2[S:9][CH:10]=[C:6]([CH2:5][C:1]#[N:2])[C:7]=2[CH:14]=1

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 136425923-(Bromomethyl)-5-fluoro-1-benzothiophene

Product 1

HCID 18518168HCID 18518168, compoundYield 110.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

50% NaCN solution (443 mg, 9.05 mmol) in water (2 mL) was added drop wise to a solution of 3-bromomethyl-5-fluoro-benzo[b]thiophene (I-45a: 1.3 g, 3.32 mmol) in DMF (10 mL) over a period of 5 minutes at 0° C. The resulting reaction mass was stirred at room temperature for 2 hours. The reaction was monitored by TLC (5% ethylacetate in hexane). The reaction mass was quenched with sodium hypochlorite solution and extracted with ethyl acetate. The organic layer was washed with water, brine solution, dried over anhydrous sodium sulphate and concentrated. Purification by column chromatography on silica gel (6% ethylacetate in hexane) afforded 700 mg of the product (68.89% yield).

Workup

  1. customThe resulting reaction mass
  2. customThe reaction mass was quenched with sodium hypochlorite solution
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water, brine solution
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated
  7. customPurification by column chromatography on silica gel (6% ethylacetate in hexane)

Sources & evidence

ORD record
ord-6d6d55bc398243168adf19984f826520
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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