1-(2-broMophenyl)prop-2-en-1-ol synthesis

5synthesis methods

Product Name:1-(2-broMophenyl)prop-2-en-1-ol
CAS Number:114837-50-2
Molecular formula:C9H9BrO
Molecular Weight:213.07

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Yield:114837-50-2 91%

Reaction Conditions:

Stage #1: ortho-bromobenzaldehyde;allylmagnesium bromide in tetrahydrofuran at -18 - 20; for 17 h;
Stage #2: with water;ammonium chloride in tetrahydrofuran;

Steps:

1

To a solution of allylmagnesium bromide (108 mL, 108 mmol, 2.0 eq) in THF was added a solution of 2-bromobenzaldehyde (10 g, 54 mmol, 1.0 eq) in THF (20 mL) dropwise at -18⁰C. The mixture was allowed to reach room temperature for 17 h, then, quenched with saturated NH₄Cl aqueous. The mixture was partitioned between brine and ethyl acetate. The organic layer was washed with brine, dried over Na₂SO₄, filtered and concentrated. The residue was purified by column chromatography to provide l-(2-bromophenyl)prop-2-en-l-ol (10.5 g, 91%). LC-MS (m/z) = 213.0 [M + H]⁺.

References:

WO2011/19405,2011,A1 Location in patent:Page/Page column 207