4-Bromo-1-fluoro-2-methoxybenzene → 1-(4-Fluoro-3-methoxyphenyl)-4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazine

HRID 1850445Notes

Reaction equation

HRID 1850445 reaction equation
Cl.[CH3:2][C:3]1([CH3:21])[CH2:7][C:6]2[C:8]([CH3:20])=[C:9]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[C:10]([CH3:13])=[C:11]([CH3:12])[C:5]=2[O:4]1.Br[C:23]1[CH:28]=[CH:27][C:26]([F:29])=[C:25]([O:30][CH3:31])[CH:24]=1>>[F:29][C:26]1[CH:27]=[CH:28][C:23]([N:17]2[CH2:16][CH2:15][N:14]([C:9]3[C:10]([CH3:13])=[C:11]([CH3:12])[C:5]4[O:4][C:3]([CH3:21])([CH3:2])[CH2:7][C:6]=4[C:8]=3[CH3:20])[CH2:19][CH2:18]2)=[CH:24][C:25]=1[O:30][CH3:31]

Participants

3

Reactant 2

HCID 136049094-Bromo-1-fluoro-2-methoxybenzeneHCID 667599811-(2,2,4,6,7-Pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazine hydrochloric acid salt

Product 1

HCID 594850061-(4-Fluoro-3-methoxyphenyl)-4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazineYield 53.2%

Procedure

By using 1-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazine hydrochloric acid salt (311 mg, 1.00 mmol) synthesized in Reference example 147 and 4-bromo-1-fluoro-2-methoxybenzene (308 mg, 1.50 mmol), the reaction was carried out in the same manner as Example 23 to synthesize the title compound 212 mg (yield 53%). Melting point was 152 to 155° C. (hexane).

Sources & evidence

ORD record
ord-be1a1a02ec7f41a9a95b47b286911b96
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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