4-Bromobenzoyl chloride → (4-Bromo-phenyl)-(2-butyl-benzofuran-3-yl)-methanone

HRID 1782665Notes

Reaction equation

HRID 1782665 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[CH:9]=1)[CH2:2][CH2:3][CH3:4].[Br:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1.[Al+3].[Cl-].[Cl-].[Cl-]>ClCCl>[Br:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH2:1][CH2:2][CH2:3][CH3:4])=[O:20])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 685154-Bromobenzoyl chlorideHCID 779512-ButylbenzofuranHCID 6451240Aluminum(III) Chloride

Product 1

HCID 59655974(4-Bromo-phenyl)-(2-butyl-benzofuran-3-yl)-methanoneYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-n-butylbenzofurane (19.8 g, 114 mmol) and 4-bromobenzoyl chloride (25.0 g, 114 mmol) in dry dichloromethane (300 mL, 0.4 M) was cooled to 0° C. and treated with AlCl3 (16.6 g, 1.1 equiv., 125.4 mmol) in 3 portions. After the additions were complete, the solution was stirred for 3 h and carefully added to ice water. After separation, the aqueous layer was extracted with dichloromethane (2×200 mL) and the combined organic layers were washed with water, sat'd aq NaCl, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification by flash column chromatography (1-2% ethyl acetate in heptane) afforded (4-bromo-phenyl)-(2-butyl-benzofuran-3-yl)-methanone (14.6 g, 36%).

Workup

  1. customAfter separation
  2. extractionthe aqueous layer was extracted with dichloromethane (2×200 mL)
  3. washthe combined organic layers were washed with water
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash column chromatography (1-2% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-58f58401393a45d59b85a43a7bd85fc0
Source dataset
uspto-grants-2009_03
Patent number
US07498356B2

Reaction notes

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