Dimethyl Sulfoxide → HCID 85603868, compound
Reaction equation
[C:1](I)([C:4]([C:7]([C:10]([C:13]([C:16]([C:19]([C:22]([C:25]([C:28]([F:31])([F:30])[F:29])([F:27])[F:26])([F:24])[F:23])([F:21])[F:20])([F:18])[F:17])([F:15])[F:14])([F:12])[F:11])([F:9])[F:8])([F:6])[F:5])([F:3])[F:2].Br[C:34]1[CH:39]=[C:38]([CH3:40])[CH:37]=[CH:36][C:35]=1[CH3:41].CS(C)=O.[I-].[K+]>[Cu].ClCCl>[F:2][C:1]([F:3])([C:34]1[CH:39]=[C:38]([CH3:40])[CH:37]=[CH:36][C:35]=1[CH3:41])[C:4]([F:6])([F:5])[C:7]([F:9])([F:8])[C:10]([F:12])([F:11])[C:13]([F:15])([F:14])[C:16]([F:18])([F:17])[C:19]([F:21])([F:20])[C:22]([F:24])([F:23])[C:25]([F:27])([F:26])[C:28]([F:31])([F:30])[F:29]Participants
Procedure
A solution of C10F21I(4.2 g, 6.5 mmol) was added dropwise over 10 min to a stirred mixture of 2-bromo-ρ-xylene (1 g, 5.4 mmol), copper powder (1.9 g, 29.7 mmol), DMSO (80 mL) at 130° C. The reaction mixture was subsequently stirred for a further 2 d at this temperature. After cooling to room temperature, it was poured into a beaker containing dichloromethane (50 mL) and saturated potassium iodide solution (50 mL). After filtering, the organic layer was separated, washed with water (3×30 mL) and dried over MgSO4. Recrystallization from hexane gave the product 15 as a white solid (2.7 g, 82%): 1H NMR (300 MHz, CDCl3): 7.31 (1H, s), 7.24 (1H, d, J=8.1 Hz)), 7.17 (1H, d, J=8.1 Hz)), 2.46 (3H, t, J=3.0 Hz)), 2.39 (3H, s); 19F NMR (282 MHz, CDCl3): −81.4, −106.7, −121.1, −121.8, −122.0, −122.9, −126.3; HR-MS (EI) calcd. for C18H9F21 (M+): 624.0363, found: 624.0353.
Workup
- additionit was poured into a beaker
- filtrationAfter filtering
- customthe organic layer was separated
- washwashed with water (3×30 mL)
- dry with materialdried over MgSO4
- customRecrystallization from hexane
Sources & evidence
- ORD record
- ord-1a042d280fa646de98d4bd808d78f97f
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07700366B2
Reaction notes
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