Thionyl Chloride → 2-(3-Bromo-4-methylphenyl)-4,4-dimethyl-4,5-dihydrooxazole
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[CH3:16])[C:5]([NH:7][C:8]([CH3:12])([CH3:11])[CH2:9][OH:10])=O.S(Cl)(Cl)=O>C(OCC)C>[Br:1][C:2]1[CH:3]=[C:4]([C:5]2[O:10][CH2:9][C:8]([CH3:12])([CH3:11])[N:7]=2)[CH:13]=[CH:14][C:15]=1[CH3:16]Participants
Procedure
3-bromo-N-(1-hydroxy-2-methylpropan-2-yl)-4-methylbenzamide (1.7 g, 6.04 mmol, 1.0 eq) was treated with thionyl chloride (0.9 mL, 12.08 mmol, 2.0 eq) and the neat reaction mixture was stirred at room temperature for 12 h. The mixture is diluted with diethyl ether (50 mL) and the precipitated solid was filtered and washed with diethyl ether (20 mL). The solid collected was dissolved in sodium hydroxide solution (1N, 15 mL) and extracted with diethyl ether (2×20 mL). The combined organic layers were washed with brine (20 mL), dried (Na2SO4) and filtered. The filtrate was concentrated under vacuum to afford the 1.0 g of the desired title product as a white solid. 1HNMR (400 MHz, CDCl3) δ 8.12 (d, J=1.0 Hz, 1H), 7.75 (dd, J=1.0, 8.0 Hz, 1H), 7.25 (d, J=8.0 Hz, 1H), 4.09 (s, 2H), 2.42 (s, 3H), 1.37 (s, 6H); ESI-MS (m/z) 268, 270 [(MH)+, Br79,81].
Workup
- filtrationthe precipitated solid was filtered
- washwashed with diethyl ether (20 mL)
- customThe solid collected
- dissolutionwas dissolved in sodium hydroxide solution (1N, 15 mL)
- extractionextracted with diethyl ether (2×20 mL)
- washThe combined organic layers were washed with brine (20 mL)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationThe filtrate was concentrated under vacuum
Sources & evidence
- ORD record
- ord-6196c072b26e4dd7acdcaa4ba2e5c976
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09169242B2
Reaction notes
Loading…