Boron trifluoride etherate → HCID 68015074, compound

HRID 1913024Notes

Reaction equation

HRID 1913024 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:19])=[C:6]([CH:8]([C:10]2[CH:11]=[CH:12][C:13]3[O:17][CH2:16][CH2:15][C:14]=3[CH:18]=2)O)[CH:7]=1.C([SiH](CC)CC)C.B(F)(F)F.CCOCC>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:19])=[C:6]([CH2:8][C:10]2[CH:11]=[CH:12][C:13]3[O:17][CH2:16][CH2:15][C:14]=3[CH:18]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 61099758HCID 61099758, compound

Product 1

HCID 68015074HCID 68015074, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(5-bromo-2-chloro-phenyl)-(2,3-dihydrobenzofuran-5-yl)methanol 5c (10.5 g, 30.9 mmol) was dissolved in 100 mL dichloromethane, followed by addition of triethylsilane (14.8 mL, 92.7 mmol) and dropwise addition of boron trifluoride etherate (7.8 mL, 61.8 mmol). The reaction mixture was stirred for 16 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-[(5-bromo-2-chloro-phenyl)methyl]-2,3-dihydrobenzo-furan 5d (10.0 g, pale yellow grease), yield: 100%. 1H NMR (400 MHz, CDCl3): δ 7.29-7.21 (m, 3H), 7.00 (s, 1H), 6.93 (d, 1H), 6.73 (d, 1H), 4.56 (t, 2H), 3.98 (s, 2H), 3.18 (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-307e8bf3858745f682c59c4bb13e3838
Source dataset
uspto-grants-2013_12
Patent number
US08609622B2

Reaction notes

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