Pyridine → HCID 86588385, compound
Reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:9]([CH3:12])([CH3:11])[CH3:10])=[C:6]([OH:8])[CH:7]=1.[CH3:13][C:14](C)([O-])C.[K+].F[C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][C:21]=1[N+]([O-])=O.N1C=CC=C[CH:31]=1>>[C:9]([C:5]1[CH:4]=[CH:3][C:2]([C:13]#[CH:14])=[CH:7][C:6]=1[O:8][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH3:31])=[CH:22][CH:21]=1)([CH3:12])([CH3:11])[CH3:10]Participants
Procedure
Employing the same general procedure as for the preparation of 2-tert-butyl-5-trimethylsilanylethynyl-1-[(4'-trifluoromethyl)phenoxy]benzene (Compound K), 4.0 g (17.5 mmol) of 5-bromo-2-tert-butylphenol (Compound H) was converted into crude 5-bromo-2-tert-butyl-1-[(4'-methyl-2'-nitro)phenoxy]benzene using 3.85 g (31.5 mmol) of potassium t-butoxide, 6.35 g (33.5 mmol) of cuprous iodide, 3.25 g (21.0 mmol) of 4-fluoro-3-nitrotoluene and 53 mL of pyridine. Purification by flash chromatography (silica, 1% ethyl acetate in hexane) gave crude 5-bromo-2-tert-butyl-1-[(4'-methyl-2'-nitro)phenoxy]benzene. 1.87 g (5.1 mmol) of this crude sample was converted into the title compound using 898 mg (1.3 mmol) of bis(triphenylphosphine)palladium (II) chloride, 246 mg (1.3 mmol) of cuprous iodide, 5.5 mL (5.1 g, 51.6 mmol) of trimethylsilyl acetylene and 11 mL of triethylamine. Purification by flash chromatography (preabsorbed onto silica with 100% chloroform, eluted with 1% ethyl acetate in hexane) gave the title compound as a brown semisolid.
Workup
- customPurification by flash chromatography (silica, 1% ethyl acetate in hexane)
- customgave crude 5-bromo-2-tert-butyl-1-[(4'-methyl-2'-nitro)phenoxy]benzene
Sources & evidence
- ORD record
- ord-82d1a09d43a142e6817ebb8a64d807c2
- Source dataset
- uspto-grants-1999_07
- Patent number
- US05919970
Reaction notes
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