Water → 3-(2-(Benzyloxy)-4-chlorophenyl)-5-(bromomethyl)-1,2,4-thiadiazole

HRID 453121Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C:16]1[N:20]=[C:19]([CH2:21]O)[S:18][N:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)[Br:24].O>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C:16]1[N:20]=[C:19]([CH2:21][Br:24])[S:18][N:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of (3-(2-(benzyloxy)-4-chlorophenyl)-1,2,4-thiadiazol-5-yl) methanol (0.35 g, 1.05 mmol) in toluene (10 ml) was added PBr3 (0.16 ml, 1.58 mmol) and the resulting reaction mixture was heated at 100° C. for 15 min. After the completion of the reaction (TLC monitoring), the reaction mixture was cooled to 0° C., added water (50 ml) and extracted with ethyl acetate (3×50 ml). The combined organics was washed with saturated NaHCO3 solution, dried over Na2SO4, filtered and concentrated under vacuum to get the desired product (0.33 g, 79% crude yield), that was carried forward as such for the next step. MS: 395.05 (M+H)+.

Workup

customthe resulting reaction mixture
customAfter the completion of the reaction (TLC monitoring)
temperaturethe reaction mixture was cooled to 0° C.
extractionextracted with ethyl acetate (3×50 ml)
washThe combined organics was washed with saturated NaHCO3 solution
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-ce8c49171e404264b224b06ce4e20556
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492414B2

Reaction notes

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