3-Bromoanisole → HCID 20392555, compound

HRID 1045374Notes

Reaction equation

HRID 1045374 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1.C([Sn](CCCC)(CCCC)[C:15]1[O:16][CH:17]=[CH:18][N:19]=1)CCC>C1(C)C=CC=CC=1>[CH3:9][O:8][C:4]1[CH:3]=[C:2]([C:15]2[O:16][CH:17]=[CH:18][N:19]=2)[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 169713-BromoanisoleHCID 154861832-(Tri-n-butylstannyl)oxazole

Product 1

HCID 20392555HCID 20392555, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension containing 1.16 ml of 1-bromo-3-methoxybenzene (9.2 mmol), 2.12 ml of 2-(tributylstannanyl)-1,3-oxazole (5.9 mmol) and 276 mg (0.2 mmol) of tetrakis[triphenylphosphine]palladium in 50 ml of toluene is stirred overnight at reflux under argon. The toluene is evaporated off using a rotary evaporator, and the residue is then suspended in ethyl acetate. After filtering the suspension, the filtrate is evaporated to dryness and the crude product is purified by chromatography over silica gel, eluting with CH2Cl2 and then with CH2Cl2/acetone 98/2 to yield the title product in the form of an oil.

Workup

  1. temperatureat reflux under argon
  2. customThe toluene is evaporated off
  3. customa rotary evaporator
  4. filtrationAfter filtering the suspension
  5. customthe filtrate is evaporated to dryness
  6. customthe crude product is purified by chromatography over silica gel
  7. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-e5b61444bbdf4df597d12c6d5a909f34
Source dataset
uspto-grants-2013_10
Patent number
US08569285B2

Reaction notes

Loading…