Hydrochloric Acid → 3,5-Dibromo-4-cyanothiophene-2-carboxylic acid
Reaction equation
[Br:1][C:2]1[C:6]([C:7]#[N:8])=[C:5]([Br:9])[S:4][C:3]=1[C:10]([O:12]CC)=[O:11].O1CCCC1.CO.[OH-].[Na+].O.Cl>>[Br:1][C:2]1[C:6]([C:7]#[N:8])=[C:5]([Br:9])[S:4][C:3]=1[C:10]([OH:12])=[O:11]Participants
7
Procedure
Ethyl 3,5-dibromo-4-cyanothiophene-2-carboxylate (6.54 g, 0.0193 mol) was dissolved in a mixture of tetrahydrofuran (40.0 mL, 0.493 mol) and methanol (20.0 mL, 0.494 mol), then sodium hydroxide in water (1.0 M, 60.0 mL, 0.0600 mol) was added at 0° C. The resulting solution was warmed to rt and stirred for 20 min. The mixture was neuturalized with hydrochloric acid in water (4.0 M, 20 mL, 0.080 mol) and extracted with 80 mL DCM twice. The combined organic layers were washed with 30 mL water, evaporated in vacuo to yield a white solid product (5.96 g, yield 99.4%). LCMS: (FA) ES−, 307, 309, 311.
Workup
- extractionextracted with 80 mL DCM twice
- washThe combined organic layers were washed with 30 mL water
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-e590ce9ea2cf46a68ea558df6ceee783
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08796268B2
Reaction notes
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