Water → HCID 68452438, compound

HRID 2085784Notes

Reaction equation

HRID 2085784 reaction equation
Br[C:2]1[S:6][C:5]2[CH:7]=[CH:8][C:9]([Cl:11])=[CH:10][C:4]=2[C:3]=1[CH3:12].O.[CH3:14][N:15](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:11][C:9]1[CH:8]=[CH:7][C:5]2[S:6][C:2]([C:14]#[N:15])=[C:3]([CH3:12])[C:4]=2[CH:10]=1

Participants

6

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 27355482-Bromo-5-chloro-3-methylbenzo[b]thiophene

Product 1

HCID 68452438HCID 68452438, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

A mixture of 2-bromo-5-chloro-3-methylbenzo(b)thiophene (1.00 g, 3.82 mmol), zinc cyanide (247 mg, 2.10 mmol), and Pd(PPh3)4 (440 mg, 0.38 mmol) in DMF (15 mL) was heated to 80° C. for 16 hours, added to water (50 mL), and extracted with 30% ethyl acetate/hexanes (3×100 mL). The combined extracts were washed with brine (20 mL), dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 10% ethyl acetate/hexanes to provide the desired product.

Workup

  1. extractionextracted with 30% ethyl acetate/hexanes (3×100 mL)
  2. washThe combined extracts were washed with brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was purified by flash column chromatography on silica gel with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-f912887180db420cbb014b28e00ee833
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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