4-chloro-2-hydroxybenzamide synthesis

2synthesis methods

Product Name:4-chloro-2-hydroxybenzamide
CAS Number:37893-37-1
Molecular formula:C7H6ClNO2
Molecular Weight:171.58

89978-92-7
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37893-37-1
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Yield:37893-37-1 89%

Reaction Conditions:

Stage #1: 4-chloro-2-methoxybenzamidewith boron tribromide in dichloromethane at -78 - 20; for 2 h;
Stage #2: with water;sodium hydrogencarbonate in dichloromethane at 0;

Steps:

4-Chloro-2-hydroxybenzamide (IV):; A solution of 4-chloro-2-methoxybenzamide (0.74 g, 3.99 mmol) in dichloromethane (50 ml) was cooled to -78⁰C followed by addition of BBr₃ (1.15 ml, 11.96 mmol) under nitrogen atmosphere. The reaction mixture was allowed to stir at room temperature for 2 h. After the completion of reaction (TLC monitoring), the solution was cooled to O⁰C and quenched with water. The resulting solution was basified by aqueous NaHCO₃ and extracted with EtOAc (3 x 100 ml). The combined organics was dried over anhydrous Na₂SO₄, filtered and concentrated to get the desired product (0.608 g, 89%). MS: 172.33 (M+H)⁺.

References:

WO2009/37485,2009,A1 Location in patent:Scheme 4

31544-40-8 Synthesis

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37893-37-1
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References

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