Potassium Carbonate → 5-(3-bromophenyl)-1,3-oxazole

HRID 1753769Notes

Reaction equation

HRID 1753769 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].CC1C=CC(S([CH2:20][N+:21]#[C-:22])(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([C:5]2[O:6][CH:22]=[N:21][CH:20]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 765833-BromobenzaldehydeHCID 161915Tosylmethyl isocyanide

Product 1

HCID 27955655-(3-bromophenyl)-1,3-oxazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(3-Bromo-phenyl)-oxazole VI-a was prepared as described for intermediate I-c using 3-Bromo-benzaldehyde (10 g, 54 mmol), TosMIC (12.7 g, 65 mmol) and K2CO3 (8.97 g) in MeOH to give the desired intermediate VI-a as a brownish solid (12.1 g, 100%). 1H NMR (300 MHz, CDCl3) δ 7.92 (s, 1H), 7.80 (s, 1H), 7.57 (d, J=7.7 Hz, 1H), 7.46 (d, J=8.0 Hz, 1H), 7.37 (s, 1H), 7.29 (d, J=7.9 Hz, 1H).

Sources & evidence

ORD record
ord-e10efe3dd5c640fb95185cacbc23ba08
Source dataset
uspto-grants-2015_10
Patent number
US09168245B2

Reaction notes

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