N-Iodosuccinimide → HCID 10927374, compound
Reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[O:15][CH2:16][CH:17]([F:19])[F:18])([CH3:4])([CH3:3])[CH3:2].[I:20]N1C(=O)CCC1=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:12])([CH3:13])[CH3:14])[CH:8]=[C:7]([I:20])[C:6]=1[O:15][CH2:16][CH:17]([F:18])[F:19])([CH3:2])([CH3:3])[CH3:4]Participants
Conditions
- Temperature
- 38 °C
Procedure
2,4-Di-tert-butyl-1-(2,2-difluoro-ethoxy)-benzene (6.75 g, 25 mmol), N-iodosuccinimide (6.74 g, 30 mmol) and p-toluenesulfonic acid monohydrate (1.90 g, 10 mmol) were combined in dichloromethane (75 mL) and heated at 38° C. for 7 h. TLC (hexanes) indicated a small amount of starting material still present and the reaction was treated with additional N-iodosuccinimde (0.33 g). After 4 h the reaction was washed with 10% Na2SO2O3 solution (50 mL). The aqueous was backwashed with dichloromethane (100 mL) and then the combined organic portions washed with water (75 mL) and the combined organic portions washed with water (100 mL), dried (MgSO4), filtered and evaporated in vacuo to provide an orange oil (9.92 g). The material was purified by flash chromatography using hexane to give 8.88 g (90%) of a light pink oil which solidified over time. 1H NMR (250 MHz, CDCl3): δ 7.66 (d, 1H, J=2.4), 7.36 (d, 1H, =2.4), 6.29 (tt, 1H, J=55.3, J=4.3), 4.24 (td, 2H, J=13.2, J=4.3), 1.40 (s, 9H), 1.29 (s, 9H).
Workup
- additionthe reaction was treated with additional N-iodosuccinimde (0.33 g)
- washAfter 4 h the reaction was washed with 10% Na2SO2O3 solution (50 mL)
- washthe combined organic portions washed with water (75 mL)
- washthe combined organic portions washed with water (100 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-52885482e1a34a3a8ae87b8aaab8e350
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07348359B2
Reaction notes
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