Boron tribromide → HCID 58156887, compound

HRID 2172163Notes

Reaction equation

HRID 2172163 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:14][C:13](=[O:15])[N:12]([C:16]3[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][CH:17]=3)[N:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].B(Br)(Br)Br>ClCCl>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[S:14][C:13](=[O:15])[N:12]([C:16]3[CH:25]=[CH:24][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=3)[N:11]=2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 66616207HCID 66616207, compound

Product 1

HCID 58156887HCID 58156887, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 4-[5-(4-isopropylphenyl)-2-oxo-1,3,4-thiadiazol-3(2H)-yl]benzoate (0.20 g, 0.56 mmol) in dichloromethane (10 mL) is then treated with boron tribromide (1M in dichloromethane, 1.7 mL, 1.7 mmol) at room temperature overnight. The volatiles are removed in vacuum and the residue is treated with water. The precipitate is collected and washed thoroughly with water to furnish the desired product, 4-[5-(4-isopropylphenyl)-2-oxo-1,3,4-thiadiazol-3(2H)-yl]benzoic acid (0.19 g, 100%), m.p. 205-208° C. 1H NMR (CDCl3, 300 MHz) δ (ppm) 1.30 (d, 6H) 2.92-3.06 (m, 1H), 7.35 (d, 2H), 7.70 (d, 2H), 8.11-8.23 (m, 4H). (ES+) m/z: 341.

Workup

  1. customThe volatiles are removed in vacuum
  2. additionthe residue is treated with water
  3. customThe precipitate is collected
  4. washwashed thoroughly with water

Sources & evidence

ORD record
ord-27290549fb0f42888869a7453f6ccc84
Source dataset
uspto-grants-2015_06
Patent number
US09051342B2

Reaction notes

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