Chlorobenzene → HCID 86700907, compound

HRID 1424364Notes

Reaction equation

HRID 1424364 reaction equation
[Cl:1][C:2]1[CH:13]=[C:12]([O:14]C)[C:5]2[CH:6]=[C:7]([C:9](=[O:11])[CH3:10])[O:8][C:4]=2[CH:3]=1.ClC1C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-]>>[Cl:1][C:2]1[CH:13]=[C:12]([OH:14])[C:5]2[CH:6]=[C:7]([C:9](=[O:11])[CH3:10])[O:8][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 7964ChlorobenzeneHCID 6451240Aluminum(III) ChlorideHCID 867009061-(6-Chloro-4-methoxy-2-benzofuranyl)ethanone

Product 1

HCID 86700907HCID 86700907, compoundYield 88%

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 1-(6-chloro-4-methoxybenzofuran-2-yl)ethanone (Example 37C, 1.43 g, 6.37 mmol) in chlorobenzene (15 mL, 148 mmol) was added aluminum chloride (3.40 g, 25.5 mmol) in portions over a period of 10 minutes. The reaction vessel was then sealed and heated at 100° C. for 40 minutes, then cool to r.t. and poured onto crushed ice (rinsed stirring bar with EtOAc). This was stirred for 30 minutes, then extracted with ethyl acetate. The organic phase was dried (MgSO4), filtered and concentrated to dryness. The residue was purified by ISCO using hexanes/EtOAc as eluent. Fractions containing the desired product were concentrated to give the title material (1.18 g, 5.60 mmol, 88% yield) as a light brown solid. LC (Method A): 1.783 min. LCMS (APCI) calcd for C10H8ClO3 [M+H]+ m/z 211.02. found 211.0. 1H NMR (CDCl3, 400 MHz) δ ppm: 11.01 (s, 1H), 7.89 (s, 1H), 6.72 (s, 1H), 2.52 (s, 3H).

Workup

  1. customThe reaction vessel was then sealed
  2. temperaturecool to r.t.
  3. additionpoured
  4. customonto crushed ice (rinsed stirring bar with EtOAc)
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic phase was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe residue was purified by ISCO
  10. additionFractions containing the desired product
  11. concentrationwere concentrated

Sources & evidence

ORD record
ord-da0f4cf96dea4c839f5e800d70a23201
Source dataset
uspto-grants-2015_01
Patent number
US08927688B2

Reaction notes

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