4-Iodo-2-methylphenol

A soln. of 2-methylphenol in methanol was treated with sodium iodide (1 mole) and sodium hydroxide (1 mole), cooled to OC sodium hypochlorite was added at 0-3C during 45min. /Uter addition of aqueous sodium thiosulphate, 4-iodo-2-methylphenol was isolated... 

Reaction of 9-fluoro-7-oxo-2,3-dihydro7H-pyrido[l,2,3-de][l,4]oxa-zine-6-carboxylate and ferf-butyl (2-mercaptoethyl)carbamate in DMSO at 100 °C for 5 h gave 9-[2-(ferc-butoxycarbonylamino)ethylthio] derivative (06WOP2006/050943). The iodo atom of 9-iodo-7-oxo-2,3-dihydro-7H-pyrido[l,2,3-de][l,4]oxazine-6-carboxylic acids was coupled with 4 -0-(2-allyloxyethyl)azithromicin in MeCONMe2 in the presence of Bu3N and fra s-di-g-acetato-bis[2-(di-o-tolylphosphino)benzyl]dipalladium(II) and di(ferf-butyl)-4-methylphenol at 110-115 °C for 15-17 h to give a mixture of 9-(3-substituted prop-1- and -2-enyl) derivatives (07WOP2007/ 054296). 10-methoxy and 10-cyano-3-hydroxymethyl-2,3-dihydro-5H-pyr-ido[l,2,3-de][l,4]benzoxazin-5-ones were obtained from 10-bromo derivative by reaction with NaOMe in the presence of Cu(I)I at 140 °C in DMF,... 

To 2-chloromcthyl-l-iodo-l-trimethylsilylpenta-l,4-diene (0.623g, 2.00mmol) in 12 was added 1.7M t-BuLi in pentane (2.35 niL, 4.0 mmol) at — 78 "C. The mixture was stirred for 20 min, then it was warmed to 25 C, poured into sat. aq NH Cl, washed with sat. aq NaHCO, dried (MgS04), and filtered. To this were added 2,6-di-ferr-butyl-4-methylphenol (8.8 mg, 0.04 mmol) and CDClj (2mL). The solution was carefully concentrated under Nj at 0 °C/0.5 Torr to about 2 mL. An additional CDClj (2 mL) was added, and the concentration process was repeated until no EtjO remained (GC and HNMR) yield 95% by HNMR. 

Butylidenebis (6-t-butyl-3-methylphenol) 4,4 -Bulylidenebis (3-me-thyl-6-t-butylpheno ). See 4,4-Butylidenebis (6-t-butyl-m-cresol) Butyl-3-iodo-2-propynylcarbamate. See lodopropynyl butylcarbamate 5-t-Butyl isophthalic acid. See 5-t-Butyl-1,3-benzenedicarboxylic acid... 

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