4-Bromo-3-fluoro-4-methylbenzhydrol synthesis

2synthesis methods

Product Name:4-Bromo-3-fluoro-4-methylbenzhydrol
CAS Number:853348-88-6
Molecular formula:C14H12BrFO
Molecular Weight:295.15

51436-99-8 Synthesis

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Yield:853348-88-6 65%

Reaction Conditions:

Stage #1: 2-fluoro-4-bromotoluenewith magnesium;iodine in tetrahydrofuran; for 1.66667 h;Heating / reflux;
Stage #2: 4-bromo-benzaldehyde in tetrahydrofuran at 0 - 20; for 2.5 h;

Steps:

1

Dried magnesium turnings (4.24 g, 0.55 mole) were stirred with a heavy stirrer bar under argon for 16 hours. A few crystals of iodine were added followed by the addition a solution of 4-bromo-2-fluorotoluene (94.5 g, 0.5 mole) in tetrahydrofuran [THF] (200ml). This addition took place over about 40 minutes and the solution was allowed to reflux during the addition. The resulting solution was stirred for 1 hour.4-Bromobenzaldehyde (71.7 g 0.39 mole) in THF (200 ml) was cooled to0 C then treated with the above Grignard solution. The addition of the Grignard solution took place over30 minutes and the resulting solution was stirred for 2 hours at room temperature. The reaction mixture was poured slowly into a solution of potassium sodium tartrate (10% solution,1 L) and extracted with ethyl acetate (EtOAc). The organic solution was dried with brine and sodium sulfate and evaporated. Trituration with hexane gave the title compound(D1) as a white solid (71.8 g, 65%). 1H NMR: aH(CDCI3) 2.20 (1 H, d), 2.24 (3H, m), 5.75(1 H, d), 6.98(1H, s) 7.05 (1H, m), 7.16 (1H, m), 7.24 (2H, m) 7.47 (2H, m).

References:

WO2005/51399,2005,A1 Location in patent:Page/Page column 21-22

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185077-02-5 Synthesis

3-FLUORO-2-METHYLPHENYLMAGNESIUM BROMID&

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References