Benzyl 2-iodo-5-methoxyphenyl sulfide → Benzyl 5-methoxy-2-(prop-1-ynyl)phenyl sulfide

HRID 218861Notes

Reaction equation

HRID 218861 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[S:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.I[C:19]1[C:24](NC(=O)C(F)(F)F)=C(OC(C)C)C(OC)=C[CH:20]=1>>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:20]#[C:19][CH3:24])=[C:3]([S:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:4]=1

Participants

3

Reactant 2

HCID 11175707Benzyl 2-iodo-5-methoxyphenyl sulfideHCID 866376576-iodo-2-isopropoxy-3-methoxy-N-trifluoroacetylaniline

Product 1

HCID 67287314Benzyl 5-methoxy-2-(prop-1-ynyl)phenyl sulfideYield 69%

Procedure

When benzyl 2-iodo-5-methoxyphenyl sulfide (Flynn et al, Org. Lett. 2001, 3(5), 651) was substituted for 6-iodo-2-isopropoxy-3-methoxy-N-trifluoroacetylaniline in Step C of Example 38 and reaction time was extended to 72 h, the similar process provided the title compound in 69% yield as a creamy solid. 1H-NMR (CDCl3) 2.1 (s, 2H); 3.7 (s, 3H); 4.17 (s, 2H); 6.61 (dd, 1H, J=2.53, 8.5 Hz); 6.72 (d, 1H, J=2.53 Hz); 7.2-7.33 (m, 5H); 7.38 (d, 1H, J=8.5 Hz).

Sources & evidence

ORD record
ord-f70f1a0575d34b5abeca5b532d36d3a5
Source dataset
uspto-grants-2012_06
Patent number
US08198466B2

Reaction notes

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