Bromine → HCID 67516471, compound

HRID 2173205Notes

Reaction equation

HRID 2173205 reaction equation
[CH3:1][C:2]1[C:9]2[CH2:8][O:7][C:6](=[O:10])[C:5]=2[S:4][CH:3]=1.[Br:11]Br>C(Cl)(Cl)Cl.ClCCl>[Br:11][C:3]1[S:4][C:5]2[C:6](=[O:10])[O:7][CH2:8][C:9]=2[C:2]=1[CH3:1]

Participants

5

Reactant 2

HCID 24408BromineHCID 67516338HCID 67516338, compound

Product 1

HCID 67516471HCID 67516471, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 6344DichloromethaneSolvent

Procedure

In a 50 mL round bottom flask was added 3-methylthieno[2,3-c]furan-6-(4H)-one (130 mg, 0.843 mmol, 1.0 eq) and chloroform (5 mL). To above solution was added bromine (86 μL, 1.08 mmol, 2.0 eq) in chloroform. The reaction was heat to reflux for 3 hr, cooled down, diluted with dichloromethane, washed with water, diluted sodium thiosulfate. The organic phase was dried over MgSO4, filtered and concentrated. The desired product was obtained after purification by flash column chromatography. LC-MS (IE, m/z): 235.2 [M+1]+; 1H NMR (500 MHz, CDCl3, δ in ppm): 5.16 (2H, s), 2.19 (3H, s);

Workup

  1. temperatureThe reaction was heat
  2. temperatureto reflux for 3 hr
  3. temperaturecooled down
  4. washwashed with water, diluted sodium thiosulfate
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-93b04947ae8e4f46bded7751ee0ace81
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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