Carbon tetrabromide → HCID 22731093, compound

HRID 2085371Notes

Reaction equation

HRID 2085371 reaction equation
[C:1]([Br:5])(Br)(Br)[Br:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:25]([C:27]1[O:28][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:30][N:31]=1)=O>C(Cl)Cl>[Br:2][C:1]([Br:5])=[CH:25][C:27]1[O:28][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:30][N:31]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 227310862-Oxazolecarboxaldehyde, 5-(1,1-dimethylethyl)- (9CI)

Product 1

HCID 22731093HCID 22731093, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of carbon tetrabromide (24.0 g, 72.4 mmole) in methylene chloride (200 mL) at 5-10 deg C. under argon atmosphere was added triphenylphosphine (37.0 g, 141 mmole) in portions. The reaction mixture was stirred for 5 min and treated with a solution of 2-formyl-5-t-butyloxazole in methylene chloride (60 mL). The reaction mixture was stirred at room temperature for 2 hours, while a white solid precipitated out of the solution. The solid was filtered off, the filtrate concentrated and purified (silica gel, EtOAc/hexane 1:4) to give 1,1-dibromo-2-(5-t-butyl-oxazol-2-yl)ethylene as a pale solid (9.13 g, 39%).

Workup

  1. customat 5-10 deg C
  2. stirringThe reaction mixture was stirred at room temperature for 2 hours, while a white solid
  3. customprecipitated out of the solution
  4. filtrationThe solid was filtered off
  5. concentrationthe filtrate concentrated
  6. custompurified (silica gel, EtOAc/hexane 1:4)

Sources & evidence

ORD record
ord-44a17eac28cc465a980d6efcc76bf141
Source dataset
uspto-grants-2004_04
Patent number
US06720347B2

Reaction notes

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