Acetic Acid Mixture with Hydrobromic Acid → 1-(2-Bromomethyl-3-cyclopropylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one

HRID 628493Notes

Reaction equation

CO[CH2:3][C:4]1[C:9]([CH:10]2[CH2:12][CH2:11]2)=[CH:8][CH:7]=[CH:6][C:5]=1[N:13]1[C:17](=[O:18])[N:16]([CH3:19])[N:15]=[N:14]1.[BrH:20].C(O)(=O)C>C(O)(=O)C>[Br:20][CH2:3][C:4]1[C:9]([CH:10]2[CH2:12][CH2:11]2)=[CH:8][CH:7]=[CH:6][C:5]=1[N:13]1[C:17](=[O:18])[N:16]([CH3:19])[N:15]=[N:14]1

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 1-(2-methoxymethyl-3-cyclopropylphenyl)-4-methyl-1,4-dihydrotetrazole-5-one (described in Reference Preparation example 7) 26.0 g, acetic acid 40 ml and 25% hydrogen bromide-acetic acid solution 40 ml was stirred at 65° C. for two hours. To the reaction mixture was added saturated saline, and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with aqueous saturated sodium bicarbonate solution and was dried over anhydrous sodium sulfate. The mixture was concentrated under reduced pressure to give 1-(2-bromomethyl-3-cyclopropylphenyl)-4-methyl-1,4-dihydrotetrazole-5-one 30.8 g.

Workup

additionTo the reaction mixture was added saturated saline
extractionthe reaction mixture was extracted with ethyl acetate
washThe organic layer was washed with aqueous saturated sodium bicarbonate solution
dry with materialwas dried over anhydrous sodium sulfate
concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-0d7493253b994d529661e678f9b24929
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09314023B2

Reaction notes

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