Boron trifluoride etherate → HCID 22613096, compound

HRID 844367Notes

Reaction equation

HRID 844367 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)O)[CH:5]=[C:6]([O:13][CH3:14])[C:7]=1[O:8][CH2:9][CH2:10][O:11][CH3:12].C([SiH](CC)CC)C.B(F)(F)F.CCOCC>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:15][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:5]=[C:6]([O:13][CH3:14])[C:7]=1[O:8][CH2:9][CH2:10][O:11][CH3:12]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 22613112HCID 22613112, compound

Product 1

HCID 22613096HCID 22613096, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 500 mL round bottomed flask with a stirring bar and a nitrogen inlet was added of 1-(3-bromo-4-(2-methoxyethoxy)-5-methoxyphenyl)-1-phenylmethanol (12.83 g, 34.94 mmol), dry methylene chloride (200 mL) and triethylsilane (13.87 mL, 87.34 mmol). This solution was cooled in an ice bath and borontrifluoride etherate (4.43 mL, 34.94 mmol) was added with a syringe over 5 min. The mixture was aged 2 h at 0° C. The reaction was quenched with saturated aqueous sodium bicarbonate solution and the mixture was extracted with chloroform. The chloroform fraction was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. This material was chromatographed on 400 g of silica gel using 20/80 EtOAc-hexane as eluant to give 9.45 g of 1-(3-bromo-4-(2-methoxyethoxy)-5-methoxyphenyl)-1-phenylmethane as an oil. 1H NMR (CDCl3): δ3.44 (s, 3H); 3.74 (t, j=4 Hz, 2H); 3.77 (s, 3H); 3.88 (s, 2H); 4.13 (t, j=4 Hz, 2H); 6.64 (d, j=2Hz, 1H); 6.94 (d, j=2Hz, 1H); 7.26 (m, 5H).

Workup

  1. temperatureThis solution was cooled in an ice bath
  2. customThe reaction was quenched with saturated aqueous sodium bicarbonate solution
  3. extractionthe mixture was extracted with chloroform
  4. washThe chloroform fraction was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThis material was chromatographed on 400 g of silica gel using 20/80 EtOAc-hexane as eluant

Sources & evidence

ORD record
ord-74ce35062ab3448a86c77281bddd7148
Source dataset
uspto-grants-2002_04
Patent number
US06380249B1

Reaction notes

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