4-Chloro-3,5-dinitrobenzotrifluoride → 2,6-Dinitro-1-(2-phenylchroman-6-yloxy)-4-trifluoromethylbenzene

HRID 31235

Reaction equation

HRID 31235 reaction equation
[N+](C1C=CC=CC=1OC1C=C2C(=CC=1)OC(C1C=CC=CC=1)CC2)([O-])=O.[OH:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[O:34][CH:33]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:32][CH2:31]2.[OH-].[K+].Cl[C:47]1[C:52]([N+:53]([O-:55])=[O:54])=[CH:51][C:50]([C:56]([F:59])([F:58])[F:57])=[CH:49][C:48]=1[N+:60]([O-:62])=[O:61]>CS(C)=O>[N+:53]([C:52]1[CH:51]=[C:50]([C:56]([F:57])([F:58])[F:59])[CH:49]=[C:48]([N+:60]([O-:62])=[O:61])[C:47]=1[O:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[O:34][CH:33]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:32][CH2:31]2)([O-:55])=[O:54]

Participants

6

Reactant 4

HCID 98094-Chloro-3,5-dinitrobenzotrifluorideHCID 14797Potassium HydroxideHCID 179784752-Nitro-1-(2-phenylchroman-6-yloxy)-benzeneHCID 212875382-Phenylchroman-6-ol

Product 1

HCID 179785802,6-Dinitro-1-(2-phenylchroman-6-yloxy)-4-trifluoromethylbenzene

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2,6-Dinitro-1-(2-phenylchroman-6-yloxy)-4-trifluoromethylbenzene was prepared as described for 2-nitro-1-(2-phenylchroman-6-yloxy)-benzene in Example 29(a) except that 6-hydroxyflavane (0.453 g) was used in 10 ml of dry DMSO under nitrogen. Also KI (0.498 g) and KOH (0.224 g) and 4-chloro-3,5-dinitro benzotrifluoride (0.541 mg) were added in similar manner. 1H-NMR (400 MHz; d6-DMSO): δ 8.87 (s, 2H), 7.46-7.29 (m, 5H), 6.89-6.75 (m, 4H), 5.09 (dd, 1H, J=10.3 Hz, J=2.1 Hz), 2.98-2.85 (m, 1H), 2.75-2.62 (m, 1H), 2.19-2.08 (m, 1H), 2.03-1.88 (m, 1H).

Sources & evidence

ORD record
ord-b57e550b989e402ebe3728bbf7c47b04
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Linked notes

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