1-broMo-4-(3-chloropropyl)benzene synthesis
- Product Name:1-broMo-4-(3-chloropropyl)benzene
- CAS Number:74003-34-2
- Molecular formula:C9H10BrCl
- Molecular Weight:233.53
91763-35-8
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74003-34-2
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Yield:74003-34-2 99%
Reaction Conditions:
with thionyl chloride in N,N-dimethyl-formamide at 0 - 20; for 19 h;
Steps:
1-Bromo-4-(3-chloropropyl)benzene (114)
3-(4-Bromophenyl)propan-1-ol (88) (3.5 g, 15 mmol, 1.0 eq) was dissolved in DMF (30 mL). The solution was cooled to 0°C and thionyl chloride (2.36 mL, 32.54 mmol, 2.2 eq) was added and the resulting mixture stirred for 19 h at RT. The mixture was quenched with H2O (1x100 mL) and washed with H2O (2x100 mL). The phases were separated and the combined aqueous layers were extracted with Et2O (2x100 mL). The combined organic layers were dried over Na2SO4, filtered and the solvent removed under reduced pressure. The resulting residue was purified via flash-column-chromatography (SiO2, 100% pentane) to yield the product (3.75 g, 99%). 1H NMR (300 MHz, chloroform-d) δ 7.46 - 7.37 (m, 2H), 7.08 (d, J = 8.4 Hz, 2H), 3.51 (t, J = 6.4 Hz, 2H), 2.74 (t, J = 7.4 Hz, 2H), 2.12 - 1.98 (m, 2H). 13C NMR (75 MHz, chloroform-d) δ 139.74, 131.68, 130.44, 120.04, 44.11, 33.90, 32.24.
References:
Grimm, Sebastian H.;Gagestein, Berend;Keijzer, Jordi F.;Liu, Nora;Wijdeven, Ruud H.;Lenselink, Eelke B.;Tuin, Adriaan W.;van den Nieuwendijk, Adrianus M.C.H.;van Westen, Gerard J.P.;van Boeckel, Constant A.A.;Overkleeft, Herman S.;Neefjes, Jacques;van der Stelt, Mario [Bioorganic and Medicinal Chemistry,2019,vol. 27,# 5,p. 692 - 699] Location in patent:supporting information
1643-30-7
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35656-89-4
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$25.00/1g
74003-34-2
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