(S)-1-iodo-3-phenyl-3-propanol → (1R)-4-Fluoro-7-(3-iodo-1-phenyl-propoxy)-2,3-dihydrobenzo[b]thiophene

HRID 2218103Notes

Reaction equation

HRID 2218103 reaction equation
[I:1][CH2:2][CH2:3][C@@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5].[F:12][C:13]1[C:21]2[CH2:20][CH2:19][S:18][C:17]=2[C:16](O)=[CH:15][CH:14]=1>>[F:12][C:13]1[C:21]2[CH2:20][CH2:19][S:18][C:17]=2[C:16]([O:5][C@@H:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:3][CH2:2][I:1])=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 14476876(S)-1-iodo-3-phenyl-3-propanolHCID 17981923HCID 17981923, compound

Product 1

HCID 58612390(1R)-4-Fluoro-7-(3-iodo-1-phenyl-propoxy)-2,3-dihydrobenzo[b]thiophene

Procedure

using (S)-1-iodo-3-phenyl-3-propanol with 4-fluoro-2,3-dihydrobenzo[b]thiophen-7-ol, to give 243 mg of the title compound as a colourless solid: δH (300 MHz, CDCl3) 7.32-7.12 (5H, m, 3-ArH), 6.46-6.27 (3H, m, ArH), 5.15-5.06 (1H, m, CHO), 3.43-3.11 (6H, m CH2CH2HI and SCH2CH2), 2.50-2.31 (1H, m, CHHCH2I) and 2.27-2.09 (1H, m, CHHCH2I).

Sources & evidence

ORD record
ord-bee28b402d5b46a6a61de23fb34f327f
Source dataset
uspto-grants-2008_08
Patent number
US07410982B2

Reaction notes

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