5-Bromo-2-fluorotoluene → 1-(4-Fluoro-3-methylphenyl)-4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazine

HRID 1850442Notes

Reaction equation

HRID 1850442 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:6][C:5]2[C:7]([CH3:19])=[C:8]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[C:9]([CH3:12])=[C:10]([CH3:11])[C:4]=2[O:3]1.Br[C:22]1[CH:23]=[CH:24][C:25]([F:29])=[C:26]([CH3:28])[CH:27]=1>>[F:29][C:25]1[CH:24]=[CH:23][C:22]([N:16]2[CH2:15][CH2:14][N:13]([C:8]3[C:9]([CH3:12])=[C:10]([CH3:11])[C:4]4[O:3][C:2]([CH3:20])([CH3:1])[CH2:6][C:5]=4[C:7]=3[CH3:19])[CH2:18][CH2:17]2)=[CH:27][C:26]=1[CH3:28]

Participants

3

Reactant 2

HCID 1235275-Bromo-2-fluorotolueneHCID 667597311-(2,2,4,6,7-Pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazine

Product 1

HCID 594850331-(4-Fluoro-3-methylphenyl)-4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazineYield 60.4%

Procedure

By using 1-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazine (311 mg, 1.0 mmol) synthesized in Reference example 61 and 5-bromo-2-fluorotoluene (0.191 mL, 1.5 mmol), the reaction was carried out in the same manner as Example 23 to synthesize the title compound 231 mg (yield 60%).

Sources & evidence

ORD record
ord-e8a63c83a88748fd94ae94effa613c06
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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