Phenylboronic Acid → 4-broMo-2-phenylthiazole

HRID 1527612Notes

Reaction equation

HRID 1527612 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:11]1[S:12][CH:13]=[C:14]([Br:16])[N:15]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]1([C:11]2[S:12][CH:13]=[C:14]([Br:16])[N:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 66827Phenylboronic AcidHCID 27632972,4-Dibromo-1,3-thiazole

Product 1

HCID 118315284-broMo-2-phenylthiazoleYield 71.8%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

A flask containing 238 mg of tetrakis(triphenylphosphine)palladium, 0.55 g of phenylboronic acid, and 1.00 g of 2,4-dibromothiazole was purged with nitrogen and then charged with 30 ml of toluene, 6.1 ml of ethanol, and 9.1 ml of a 2 M aqueous solution of sodium carbonate, and the mixture was stirred under reflux for 6 hours. After cooling to room temperature, 50 ml of water was added to the reaction mixture and two extractions were conducted with 50 ml of ethyl acetate. After being washed with 30 ml of saturated brine, the organic layer was dried over magnesium sulfate. After filtering the magnesium sulfate, the organic layer was concentrated and the residue was purified by column chromatography (Wakogel C-200; hexane:ethyl acetate=14:1) to give 0.71 g of 2-phenyl-4-bromothiazole.

Workup

  1. customwas purged with nitrogen
  2. additioncharged with 30 ml of toluene, 6.1 ml of ethanol, and 9.1 ml of a 2 M aqueous solution of sodium carbonate
  3. temperatureunder reflux for 6 hours
  4. addition50 ml of water was added to the reaction mixture and two extractions
  5. washAfter being washed with 30 ml of saturated brine
  6. dry with materialthe organic layer was dried over magnesium sulfate
  7. filtrationAfter filtering the magnesium sulfate
  8. concentrationthe organic layer was concentrated
  9. customthe residue was purified by column chromatography (Wakogel C-200; hexane:ethyl acetate=14:1)

Sources & evidence

ORD record
ord-97e41b9088c94332b045a83619df457c
Source dataset
uspto-grants-2015_07
Patent number
US09089139B2

Reaction notes

Loading…