HCID 58960010, compound → HCID 44435668, compound

HRID 916043Notes

Reaction equation

HRID 916043 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:29])=[C:6]([C:8]([CH3:28])([CH3:27])[CH2:9][C:10]([OH:26])([C:22]([F:25])([F:24])[F:23])[CH2:11][C:12]2[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[C:13]=2[C:14]#[N:15])[CH:7]=1.[F:30][C:31]1[CH:32]=[CH:33][C:34]([OH:58])=[C:35]([C:37]([CH3:57])([CH3:56])[CH2:38][C:39]([OH:55])([C:51]([F:54])([F:53])[F:52])[CH2:40][C:41]2[CH:48]=[C:47]([CH3:49])[C:44]([C:45]#[N:46])=[C:43]([CH3:50])[CH:42]=2)[CH:36]=1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:29][CH3:31])=[C:6]([C:8]([CH3:27])([CH3:28])[CH2:9][C:10]([OH:26])([C:22]([F:25])([F:24])[F:23])[CH2:11][C:12]2[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[C:13]=2[C:14]#[N:15])[CH:7]=1.[F:30][C:31]1[CH:32]=[CH:33][C:34]([O:58][CH3:2])=[C:35]([C:37]([CH3:56])([CH3:57])[CH2:38][C:39]([OH:55])([C:51]([F:54])([F:53])[F:52])[CH2:40][C:41]2[CH:48]=[C:47]([CH3:49])[C:44]([C:45]#[N:46])=[C:43]([CH3:50])[CH:42]=2)[CH:36]=1

Participants

4

Reactant 2

HCID 58960010HCID 58960010, compoundHCID 58960031HCID 58960031, compound

Product 2

HCID 44435668HCID 44435668, compoundHCID 44435669HCID 44435669, compound

Procedure

The title compounds were prepared as an inseparable mixture by methods analogous to those described in Example 5 as a result of performing a Grignard reaction with a 1:1.4 mixture of 2-bromomethyl-4,6-dimethylbenzonitrile and 4-bromomethyl-2,6-dimethylbenzonitrile (prepared by N-bromosuccinimide bromination of 2,4,6-trimetbylbenzonitrile). The mixture was treated with boron tribromide according to methods analogous to those described in Example 7 followed by chromatography on a prep plate (silica gel, hexanes-isopropyl alcohol (97:3, 2×developed)) to afford 2-[4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-4,6-dimethylbenzonitrile, m.p. 136° C.-138° C., and 4-[4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-2,6-dimethylbenzonitrile, m.p. 152° C.-154° C. Methylation of 2-[4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2trifluoromethylpentyl]-4,6-dimethylbenzonitrile and 4-[4-(5 fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-2,6-dimethylbenzonitrile by analogous methods described in Example 8 gave the title compounds 2-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-4,6-dimethylbenzonitrile, m.p. 134° C.-136° C., and 4-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-2,6-dimethylbenzonitrile, m.p. 113° C.-115° C.

Sources & evidence

ORD record
ord-f35c5d6e0f29485e87109328b79ab63c
Source dataset
uspto-grants-2007_09
Patent number
US07268152B2

Reaction notes

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