Carbon tetrabromide → HCID 20721245, compound

HRID 2086206Notes

Reaction equation

HRID 2086206 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)[Br:21].[C:25]([O:29][C:30]([N:32]1[C@@:36]([CH:38]=O)([CH3:37])[CH2:35][O:34][C:33]1([CH3:41])[CH3:40])=[O:31])([CH3:28])([CH3:27])[CH3:26]>ClCCl>[C:25]([O:29][C:30]([N:32]1[C@:36]([CH:38]=[C:20]([Br:24])[Br:21])([CH3:37])[CH2:35][O:34][C:33]1([CH3:41])[CH3:40])=[O:31])([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 11139335HCID 11139335, compound

Product 1

HCID 20721245HCID 20721245, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Triphenylphosphine (17.3 g, 65.8 mmol) was dissolved in dichloromethane (25 ml), and a solution of carbon tetrabromide (10.9 g, 32.9 mmol) in dichloromethane (15 ml) was added dropwise thereto in an ice bath followed by stirring for 5 minutes in the ice bath. To the reaction solution was added dropwise a dichloromethane (40 ml) solution of 3-t-butoxycarbonyl-2,2-dimethyl-(4S)-formyl-4-methyloxazolidine (4.00 g, 16.4 mmol) obtained in Reference example 2(c). After stirring for 14 hours at room temperature, insoluble substances of the reaction mixture were filtered out, the filtrate was concentrated under reduced pressure to give the crude title compound (4.70 g, 71.2% yield) as a colorless oil.

Workup

  1. customin an ice bath followed
  2. customobtained in Reference example 2(c)
  3. filtrationinsoluble substances of the reaction mixture were filtered out
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-766312d9400c460fb4433afa0d6393f2
Source dataset
uspto-grants-2004_04
Patent number
US06723745B2

Reaction notes

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