4-(3-bromophenoxy)butanoic acid(WXC08432) synthesis
- Product Name:4-(3-bromophenoxy)butanoic acid(WXC08432)
- CAS Number:170638-88-7
- Molecular formula:C10H11BrO3
- Molecular Weight:259.1
1096893-57-0
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Yield:170638-88-7 99%
Reaction Conditions:
Stage #1: methyl 4-(3-bromophenoxy)butanoatewith water;sodium hydroxide in methanol at 65; for 0.5 h;
Stage #2: with hydrogenchloride in water; pH=~ 2;
Steps:
119.2
Step No.2: 4-(3-Bromophenoxy)butanoic acid (137)Methyl 4-(3-bromophenoxy)butanoate (136) (21.6 g, 79.0 mmol) was treated with 3 N aqueous sodium hydroxide (79 mL, 237 mmol) and MeOH (100 mL) then warmed to about 65° C. for about 30 min. The mixture was cooled to rt and concentrated under reduced pressure to remove most of the MeOH. The mixture was diluted with water (100 mL), acidified to about pH 2 with concentrated HCl then extracted with EtOAc (150 mL, then 75 mL). The combined organics were dried over MgSO4, filtered and concentrated under reduced pressure to give 4-(3-bromophenoxy)butanoic acid (137) (20.3 g, 99%). LC/MS, method 3, Rt=2.15 min, MS m/z: 257, 259 (M-H)-. 1H NMR (400 MHz, DMSO-d6) δ 12.17 (bs, 1H), 7.23 (t, J=8.1 Hz, 1H), 7.16-7.09 (m, 2H), 6.94 (ddd, J=8.3, 2.4, 0.9 Hz, 1H), 4.00 (t, J=6.4 Hz, 2H), 2.37 (t, J=7.3 Hz, 2H), 1.96-1.80 (m, 2H).
References:
US2012/238549,2012,A1 Location in patent:Page/Page column 126-127
157245-84-6
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