3-Fluoro-p-toluic acid → 3-Fluoro-5-iodo-4-methylbenzoic acid
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].[I:12]N1C(=O)CCC1=O>FC(F)(F)S(O)(=O)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:12])[C:10]=1[CH3:11])[C:5]([OH:7])=[O:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
3-Fluoro-4-methylbenzoic acid (1 g, 6.48 mmol, 1 eq) was dissolved in trifluoromethanesulphonic acid (10 ml) and the reaction was cooled to 0° C. To the above solution N-iodosuccinimide (1.46 g, 6.48 mmol, 1 eq) was added in portion and the reaction was stirred at room temperature for 14 h. Later the above solution was poured into 50 ml of ice water, the solid obtained was filtered. The solid was dissolved in ethylacetate, washed with sodiumthiosulphate solution and brine, the organic layer was concentrated to get the desired product as light brown solid. Yield: 1.5 g (83%). 1H NMR (400 MHz, CDCl3): δ 2.35 (s, 3H), 7.68 (d, 1H, J=8 Hz), 8.14 (s, 1H). 13.50 (br, 1H).
Workup
- customthe solid obtained
- filtrationwas filtered
- dissolutionThe solid was dissolved in ethylacetate
- washwashed with sodiumthiosulphate solution and brine
- concentrationthe organic layer was concentrated
Sources & evidence
- ORD record
- ord-86e046ce1bb9455e9db75cbfff23f73d
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08048887B2
Reaction notes
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