Water → 88203-23-0

HRID 2121306Notes

Reaction equation

HRID 2121306 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=3)=[N:16][N:17]=2)=[CH:9][CH:8]=1.O>ClCCl>[OH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)=[N:16][N:17]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 62686517453-03-1

Product 1

HCID 515915488203-23-0

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1M solution of boron tribromide in dichloromethane (100 cm3) is added dropwise to a solution of 2,5-bis(4-methoxyphenyl)-1,3,4-thiadiazole [J. prakt. Chem., (1 980) Vol. 322, pp. 933] (2.0 g) and dichloromethane (50 cm3) at 0° C. under an atmosphere of nitrogen. The reaction solution is stirred overnight and water (100 cm3) added. The organic layer is separated off and the aqueous layer extracted with dichloromethane (2×100 cm3). The combined organic layers are washed with brine (2×100 cm3) and then dried (MgSO4), filtered and evaporated down. The residue is purified by column chromatography on silica gel using a 9:1 hexanelethyl acetate mixture as eluent and recrystallisation from ethanol to yield 1.0 g of g 2,5-bis(4-hydroxyphenyl)-1,3,4-thiadiazole.

Workup

  1. customat 0° C.
  2. customThe organic layer is separated off
  3. extractionthe aqueous layer extracted with dichloromethane (2×100 cm3)
  4. washThe combined organic layers are washed with brine (2×100 cm3)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated down
  8. customThe residue is purified by column chromatography on silica gel using a 9:1 hexanelethyl acetate mixture as eluent
  9. customrecrystallisation from ethanol

Sources & evidence

ORD record
ord-6d8088ad241b499ca06fb36355e72ee2
Source dataset
uspto-grants-2004_02
Patent number
US06696110B1

Reaction notes

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