3-Bromodiphenyl ether → (1-(2-Methyl-4-phenylthiazol-5-yl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl 4-methylbenzenesulfonate

HRID 1855032Notes

Reaction equation

HRID 1855032 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][C:13]23[CH2:20][CH2:19][C:16](C4C=CC=C(OC5C=CC=CC=5)C=4)([CH2:17][CH2:18]2)[O:15][CH2:14]3)(=[O:10])=[O:9])=[CH:4][CH:3]=1.BrC1C=CC=C(OC2C=CC=CC=2)C=1.[CH3:48][C:49]1[S:50][CH:51]=[C:52]([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[N:53]=1>>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][C:13]23[CH2:20][CH2:19][C:16]([C:51]4[S:50][C:49]([CH3:48])=[N:53][C:52]=4[C:54]4[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=4)([CH2:17][CH2:18]2)[O:15][CH2:14]3)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 961653-Bromodiphenyl etherHCID 5843772-Methyl-4-phenyl-1,3-thiazoleHCID 90408232(1-(3-Phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl 4-methylbenzenesulfonate

Product 1

HCID 90408478(1-(2-Methyl-4-phenylthiazol-5-yl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl 4-methylbenzenesulfonate

Procedure

(1-(2-Methyl-4-phenylthiazol-5-yl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl 4-methylbenzenesulfonate was prepared using a procedure analogous to (1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl 4-methylbenzenesulfonate except that 1-bromo-3-phenoxybenzene was replaced with 2-methyl-4-phenylthiazole. The title compound was obtained (0.125 g, 0.266 mmol, 62.1% yield) as a light yellowish oil. LCMS, [M+H]+=470.1. 1H NMR (500 MHz, CDCl3) δ 7.77-7.72 (m, 2H), 7.43-7.32 (m, 7H), 3.75 (s, 2H), 3.66 (s, 2H), 2.64 (s, 3H), 2.45 (s, 3H), 2.08-1.99 (m, 2H), 1.82 (ddd, J=13.3, 11.6, 4.3 Hz, 2H), 1.61 (qd, J=7.2, 3.0 Hz, 2H), 1.43 (td, J=12.4, 4.8 Hz, 2H).

Workup

  1. custom(1-(2-Methyl-4-phenylthiazol-5-yl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl 4-methylbenzenesulfonate was prepared

Sources & evidence

ORD record
ord-f727cc11d1bf4750ab5b893c3f75b6ff
Source dataset
uspto-grants-2015_02
Patent number
US08962660B2

Reaction notes

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