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Chemical Structure| 1243451-05-9

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Product Details of [ 1243451-05-9 ]

CAS No. :1243451-05-9
Formula : C10H13BrO2
M.W : 245.11
SMILES Code : OC1=CC=CC(Br)=C1OC(C)(C)C

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Application In Synthesis of [ 1243451-05-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1243451-05-9 ]

[ 1243451-05-9 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 14381-51-2 ]
  • [ 115-11-7 ]
  • [ 1243414-06-3 ]
  • [ 1243451-05-9 ]
  • [ 1369906-10-4 ]
YieldReaction ConditionsOperation in experiment
60%; 8%; 3% With sulfuric acid; In dichloromethane; at 35℃; for 72h; In a glass pressure-bottle at ?20 to ?30 °C containing a mixture of <strong>[14381-51-2]3-bromocatechol</strong> (250 mg, 1.32 mmol), H2SO4 (trace), and CH2Cl2 (2 mL), isobutene (ca. 4 g) was condensed. After sealing the pressure-bottle with a threaded Teflon cap tipped with a Teflon-protected rubber O-ring, the mixture was heated at 35 °C. After 3 days, the tube was cooled (?20 °C) and Et3N (10 muL) was added. The residue containing unreacted starting material and O-tert-butylated products 5, 6, and 7 in 72:22:6 ratio (by 1H NMR), was purified by chromatography on silica gel eluting with hexane then hexane/EtOAc 97:3 affording in the following order 7 (12 mg, 3percent), 5 (195 mg, 60percent), and 6 (26 g, 8percent) as pure oils. 2-Bromo-6-tert-butoxyphenol (5): deltaH 1.42 (9H, s, t-Bu), 6.07 (1H, s, OH), 6.68 (1H, t, J 8.2 Hz), 6.97 (1H, dd, J 8.1 and 1.4 Hz), 7.19 (1H, dd, J 8.1 and 1.4 Hz); deltaC 28.9, 81.5, 108.4, 120.1, 121.0, 127.4, 143.0, 147.5. 3-Bromo-2- tert-butoxyphenol (6): deltaH 1.51 (9H, s, t-Bu), 5.54 (1H, s, OH), 6.81?6.93 (2H, m), 7.04?7.10 (1H,dd, J 7.3 and 2.3 Hz); 13C NMR: deltaC 29.6; 84.6; 114.7; 119.1; 124.7; 125.4; 141.4; 152.0. 1-Bromo-2,3-di-tert-butoxybenzene (7): deltaH 1.34 (9H, s, t-Bu), 1.45 (9H, s, t-Bu), 6.82 (1H, t, J 8.1 Hz), 6.97 (1H, dd, J 8.1 and 1.7 Hz), 7.27 (1H, dd, J 8.0 and 1.7 Hz); deltaC 28.8, 29.9, 81.0, 84.1, 121.4, 123.7, 124.6, 128.1, 149.1, 151.6; HRMS (ESI): MNa+, found 323.0634. C14H21O2Na79Br requires 323.0623.
 

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