Hydrochloric Acid → 2-Chloro-3-hydroxy-5-iodophenyl acetate
Reaction equation
[C:1]([O:4][C:5]1[CH:10]=[C:9]([I:11])[CH:8]=[C:7]([O:12]C(=O)C)[C:6]=1[Cl:16])(=[O:3])[CH3:2].[OH-].[Li+].Cl>O.O1CCOCC1>[C:1]([O:4][C:5]1[CH:10]=[C:9]([I:11])[CH:8]=[C:7]([OH:12])[C:6]=1[Cl:16])(=[O:3])[CH3:2]Participants
6
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 2-chloro-5-iodo-1,3-phenylene diacetate (5) (5.16 g, 14.5 mmol) and 1M lithium hydroxide (29.1 mL, 29.1 mmol) in H2O (5 mL) and dioxane (20 mL) was stirred at 60° C. for 4 h then at RT for 20 h. The reaction mixture was acidified by the addition of 1M HCl and the product was extracted with EtOAc (150 mL). The organic solution was dried over MgSO4 and the solvent was removed in vacuo. The resulting oil was slurried with 1:1 DCM: isohexanes and the solvents were removed in vacuo to yield 2-chloro-3-hydroxy-5-iodophenyl acetate (6) (4.88 g, 86%) as a brown solid: m/z 311 [M−H]− (ES−).
Workup
- waitat RT for 20 h
- extractionthe product was extracted with EtOAc (150 mL)
- dry with materialThe organic solution was dried over MgSO4
- customthe solvent was removed in vacuo
- customisohexanes and the solvents were removed in vacuo
Sources & evidence
- ORD record
- ord-edc0c41070d64205b98e788d99bcca61
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447028B2
Reaction notes
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