Benzyl Bromide → 6-(Benzyloxy)-2-chlorobenzo[d]thiazole

HRID 1487717Notes

Reaction equation

[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:9][C:10]1[S:11][C:12]2[CH:18]=[C:17]([OH:19])[CH:16]=[CH:15][C:13]=2[N:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC#N.CCOC(C)=O>[CH2:1]([O:19][C:17]1[CH:16]=[CH:15][C:13]2[N:14]=[C:10]([Cl:9])[S:11][C:12]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Benzyl bromide (0.921 g, 5.39 mmol) was added to a mixture of 2-chlorobenzo[d]thiazol-6-ol (1.00 g, 5.39 mmol) and cesium carbonate (1.76 g, 5.39 mmol) in CH3CN (15 mL). After 2 h at rt the reaction mixture was heated to 70° C. overnight. Upon cooling to rt, the reaction mixture was diluted with EtOAc (100 mL) and washed with water (3×75 mL) and brine (75 mL). The EtOAc layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The material was purified by column chromatography (0 to 8% EtOAc in Hexanes gradient), yielding 1.396 g (94%) of the title compound as a reddish, waxy solid. LC-MS: RT=10.51 min., [M+H]+=275.9. Rf=0.41 in 10% EtOAc/Hexanes.

Workup

temperatureUpon cooling to rt
washwashed with water (3×75 mL) and brine (75 mL)
dry with materialThe EtOAc layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe material was purified by column chromatography (0 to 8% EtOAc in Hexanes gradient)

Sources & evidence

ORD record: ord-9126c0fdfade4fb4bbd102dd934725be
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428522B2

Reaction notes

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