4-bromo-2,6-dimethylbenzoic acid synthesis
- Product Name:4-bromo-2,6-dimethylbenzoic acid
- CAS Number:74346-19-3
- Molecular formula:C9H9BrO2
- Molecular Weight:229.07
124-38-9
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74346-19-3
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Yield: 85%
Reaction Conditions:
Stage #1:carbon dioxide;5-bromo-2-iodo-1,3-dimethyl-benzene with isopropylmagnesium chloride in tert-butyl methyl ether at 0;Grignard Reaction;
Stage #2: with hydrogenchloride;water
Steps:
2
Example 2: Preparation of 4-bromo-2,6-dimethylbenzoic acid (B2)(B2)The title compound may be prepared according to Scheme B, as follows. A solution of 5- bromo-2-iodo-l,3-dimethyl-benzene (Bl) (1.0 mol eq) in methyl-tert-butyl ether (6.0 rel vols) may be added to iso-propylmagnesium chloride (2.0 mol eq) in methyl-tert-butyl ether (2.0 rel vols), maintaining < 0 °C. Carbon dioxide gas may be added until reaction is shown to be complete. 2N aqueous hydrochloric acid may be added (4 rel vols) to quench the reaction, the phases can be separated and the aqueous phase discarded. The product may be extracted into 1M aqueous sodium hydroxide solution (6.5 rel vols), then washed with methyl tert-butyl ether (4 rel vols). The title compound (B2) may be precipitated by the addition of 2N aq hydrochloric acid (4.5 rel vols) before being filtered, washed with water then heptane and dried to yield a white crystalline solid (85%).1H NMR (400 MHz, CDC13) δΗ 2.28 (6 H, s), 7.35 (2 H, s), 13.30 (1H, s)
References:
ASTRAZENECA AB;BOYD, Alistair;FIELDING, Mark Richard;FORD, James Gair;FRODSHAM, Lianne;GOLDEN, Michael D;LESLIE, Kevin William;MCKEEVER-ABBAS, Ben;TOMLIN, Paula WO2011/84098, 2011, A1 Location in patent:Page/Page column 6-7
110-05-4
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68837-59-2
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74346-19-3
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74346-19-3
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132949-41-8
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74346-19-3
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74346-19-3
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