1-(3-BroMophenyl)cyclopropaneMethanol synthesis

5synthesis methods

Product Name:1-(3-BroMophenyl)cyclopropaneMethanol
CAS Number:886366-33-2
Molecular formula:C10H11BrO
Molecular Weight:227.1

749928-59-4 Synthesis

Methyl 1-(3-broMophenyl)cyclopropane-1-carboxylate

749928-59-4
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886366-33-2
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Yield:886366-33-2 94%

Reaction Conditions:

with diisobutylaluminium hydride in toluene at -78 - 20;

Steps:

5.5C Example 5C: (1 -(3-Bromophenyl)cyclopropyl)methanol

Example 5C: (1 -(3-Bromophenyl)cyclopropyl)methanol j00227j Example 5B (49 mg, 0.192 mmol) was dissolved in toluene (384 .iL) and cooled to -78 °C. DIBAL-H in toluene (960 .iL, 0.960 mmol) was added, and thereaction was warmed to ambient temperature over 4h. The reaction was allowed to stir overnight. The reaction was quenched with MeOH. The reaction was then diluted with 1 N HC1 and extracted thrice with EtOAc. The combined organic extracts were washed with saturated NaHCO3, then brine, dried (Na2504), filtered, and concentrated in vacuo. The crude material was purified by silica gel column chromatography (0 to 100% EtOAcin hexanes) to yield Example SC (41 mg, 94%). 1H NMR (400 MHz, CHLOROFORMc i) ?ppm 7.50(1 H, t, J=1.76 Hz), 7.31 -7.38(1 H, m), 7.21 -7.32(1 H, m), 7.17(1 H, t, J=7.91 Hz), 3.64 (2 H, s), 2.19 (1 H, s), 0.79 -0.91 (4 H, m). 13C NMR (100 MHz, CHLOROFORM-cl) ?ppm 145.2, 132.0, 129.9, 129.6, 127.6, 122.4, 70.4, 27.8, 11.5(2 carbons).

References:

WO2014/201073,2014,A1 Location in patent:Paragraph 00227