4-Bromothioanisole → 1-[4-(Methylsulfanyl)phenyl]-4-(2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)piperazine

HRID 2063846Notes

Reaction equation

[CH3:1][CH:2]1[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:21]1[CH:26]=[CH:25][C:24]([S:27][CH3:28])=[CH:23][CH:22]=1>>[CH3:28][S:27][C:24]1[CH:25]=[CH:26][C:21]([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][CH:2]([CH3:1])[CH2:6][C:5]=4[C:7]=3[CH3:19])[CH2:18][CH2:17]2)=[CH:22][CH:23]=1

Participants

Reactant 2

HCID 660374-Bromothioanisole

HCID 667598101-(2,4,6,7-Tetramethyl-2,3-dihydro-1-benzofuran-5-yl)piperazine

Product 1

HCID 594849931-[4-(Methylsulfanyl)phenyl]-4-(2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)piperazineYield 41%

Procedure

By using 1-(2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)piperazine (130 mg, 0.50 mmol) synthesized in Reference example 56 and 4-bromothioanisole (203 mg, 1.0 mmol), the reaction was carried out in the same manner as Example 23 to obtain the title compound 78 mg (yield 41%).

Sources & evidence

ORD record: ord-d55291d1902a442f9ee0321883c38841
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288390B2

Reaction notes

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