Dihydrobenzofuran → (5-Bromo-2-chloro-phenyl)-(2,3-dihydrobenzofuran-5-yl)methanone

HRID 1913022Notes

Reaction equation

HRID 1913022 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].[O:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH2:14][CH2:13]1.[Cl-].[Cl-].[Cl-].[Al+3]>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([C:7]([C:19]2[CH:18]=[CH:17][C:16]3[O:12][CH2:13][CH2:14][C:15]=3[CH:20]=2)=[O:8])[CH:10]=1

Participants

5

Reactant 3

HCID 10329DihydrobenzofuranHCID 27568715-Bromo-2-chlorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 43378845(5-Bromo-2-chloro-phenyl)-(2,3-dihydrobenzofuran-5-yl)methanoneYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-bromo-2-chloro-benzoyl chloride 2a (10.8 g, 42.5 mmol) was dissolved in 100 mL dichloromethane, followed by addition of 2,3-dihydrobenzofuran 5a (5.11 g, 42.5 mmol) and addition of aluminum trichloride (6.8 g, 51.0 mmol) in batch. The reaction mixture was stirred for 2 hours. Thereafter, the reaction mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel chromatography with elution system D to obtain the title compound (5-bromo-2-chloro-phenyl)-(2,3-dihydrobenzofuran-5-yl)methanone 5b (10.47 g, white solid), yield: 72.9%. MS m/z (ESI): 339.0 [M+1]; 1H NMR (400 MHz, CDCl3): δ 7.73 (d, 1H), 7.58 (dd, 1H), 7.53 (dd, 1H), 7.47 (d, 1H), 7.32 (d, 1H), 6.81 (d, 1H), 4.68 (t, 2H), 3.26 (t, 2H).

Workup

  1. concentrationThereafter, the reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was purified by silica gel chromatography with elution system D

Sources & evidence

ORD record
ord-7bb3f22370384dd6a3b2bc1231815e33
Source dataset
uspto-grants-2013_12
Patent number
US08609622B2

Reaction notes

Loading…