Sulfuric Acid → 2-(4-Bromophenyl)-1,3,4-oxadiazole

HRID 1865163Notes

Reaction equation

HRID 1865163 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH2:17](OC(OCC)OCC)C>>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]2[O:7][CH:17]=[N:9][N:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 222194-BromobenzohydrazideHCID 31214Ethyl orthoformate

Product 1

HCID 7151202-(4-Bromophenyl)-1,3,4-oxadiazoleYield 89.9%

Conditions

Temperature
2.5 °C

Procedure

To a suspension of 4-bromobenzoic hydrazide (200 g) in industrial methylated spirit (700 ml) was added triethylorthoformate (309 ml), industrial methylated spirit (100 ml) and sulphuric acid (0.8 ml). The reaction mixture was heated to reflux for 1 hour. The reaction mixture was cooled to 0-5° C. and product crystallised. Product was isolated, washed and dried to yield 2-(4-bromophenyl)-1,3,4-oxadiazole (186.1 g, 89.9%). 400 MHz NMR Spectrum: (DMSOd6) 9.35 (s, 1H), 7.98 (d, 1H), 7.95 (d, 1H), 7.84 (d, 1H), 7.81 (d, 1H); Mass Spectrum MH+ 224.9663 (calc. using 79-Br) Found 224.9701.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 hour
  3. customproduct crystallised
  4. customProduct was isolated
  5. washwashed
  6. customdried

Sources & evidence

ORD record
ord-fee7d7fff28d4a59a7705338d0e3b656
Source dataset
uspto-grants-2009_12
Patent number
US07626020B2

Reaction notes

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