1,2-Dibromoethane → Thiazole, 4-[2-(2-bromoethoxy)phenyl]-2-(trifluoromethyl)-

HRID 2178651Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].[F:7][C:8]([F:22])([F:21])[C:9]1[S:10][CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[OH:20])[N:13]=1.[Br:23][CH2:24][CH2:25]Br>C(#N)C>[Br:23][CH2:24][CH2:25][O:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:12]1[N:13]=[C:9]([C:8]([F:7])([F:21])[F:22])[S:10][CH:11]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Cesium carbonate (266 mg, 0.816 mmol) was added to a solution of 2-[2-(trifluoromethyl)-1,3-thiazol-4-yl]phenol (C4) (100 mg, 0.408 mmol) and 1,2-dibromoethane (0.35 mL, 4.1 mmol) in acetonitrile (33 mL), and the mixture was heated at 70° C. for 18 hours. After cooling to room temperature, the reaction was partitioned between dichloromethane and water; the organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 10% to 30% ethyl acetate in heptane) afforded the title compound. Yield: 115 mg, 0.327 mmol, 80%. 1H NMR (400 MHz, CDCl3) δ 3.78 (br dd, J=5.5, 5.5 Hz, 2H), 4.48 (dd, J=5.7, 5.5 Hz, 2H), 6.97 (br d, J=8.4 Hz, 1H), 7.13 (ddd, J=7.7, 7.4, 1.1 Hz, 1H), 7.35 (ddd, J=8.3, 7.3, 1.8 Hz, 1H), 8.31 (dd, J=7.8, 1.8 Hz, 1H), 8.37 (s, 1H).

Workup

temperatureAfter cooling to room temperature
customthe reaction was partitioned between dichloromethane and water
dry with materialthe organic layer was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customPurification via silica gel chromatography (Gradient: 10% to 30% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-f4c96ef101464fe38dfd76c95eed57b4
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067934B2

Reaction notes

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