HCID 18761562, compound → HCID 18761594, compound
Reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][Si:13]([CH3:16])([CH3:15])[CH3:14])=[CH:7][C:6]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:26]1C=CC(C(C)(C)C)=C(OC2C=CC(CC)=CC=2)C=1>>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][Si:13]([CH3:15])([CH3:14])[CH3:16])=[CH:7][C:6]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH3:26])=[CH:20][CH:19]=1)([CH3:4])([CH3:3])[CH3:2]Participants
Procedure
Employing the same general procedure as for the preparation of 2-tert-butyl-5-trimethylsilanylethynyl-1-[(4′-methyl)phenoxy]benzene (Compound U), 52 mg (0.16 mmol) 5-bromo-2-tert-butyl-1-[(4′-ethyl)phenoxy]benzene (Compound T) was converted into the title compound using 28 mg (0.04 mmol) of bis(triphenylphosphine)palladium (II) chloride, 7 mg (0.04 mmol) of cuprous iodide, 0.2 mL (150 mg, 1.5 mmol) of trimethylsilyl acetylene and 3 mL of triethylamine. An additional 28 mg (0.04 mmol) of bis(triphenylphosphine)palladium (II) chloride, and 0.2 mL (150 mg, 1.5 mmol) of trimethylsilyl acetylene were added after 3 days of heating, and the resultant mixture was then heated at 75° C. for 4 more days. Purification by flash chromatography (preabsorbed onto silica with 100% chloroform, eluted with 100% hexane) gave the title compound as a yellow oil.
Sources & evidence
- ORD record
- ord-e4467cc504c946bcb33ce173708f1b24
- Source dataset
- uspto-grants-2003_12
- Patent number
- US06660755B2
Reaction notes
Loading…