Carbon tetrabromide → HCID 24785042, compound

HRID 1717518Notes

Reaction equation

HRID 1717518 reaction equation
[C:1]([Br:5])(Br)(Br)Br.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[F:25][C:26]1[CH:27]=[CH:28][C:29]([O:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)=[C:30]([N:32]([CH2:36][C:37]2[CH:42]=[C:41]([O:43][CH3:44])[CH:40]=[CH:39][C:38]=2[O:45][CH2:46]CO)[C:33](=[O:35])[CH3:34])[CH:31]=1>CCOCC>[F:25][C:26]1[CH:27]=[CH:28][C:29]([O:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)=[C:30]([N:32]([CH2:36][C:37]2[CH:42]=[C:41]([O:43][CH3:44])[CH:40]=[CH:39][C:38]=2[O:45][CH2:46][CH2:1][Br:5])[C:33](=[O:35])[CH3:34])[CH:31]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 24785043HCID 24785043, compound

Product 1

HCID 24785042HCID 24785042, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 1.69 g (5.1 mmol) CBr4 and 2.89 g (11 mmol) PPh3 in dry dichloromethane (35 mL) 2.04 g (4.8 mmol) (1e) was added at 0° C. The reaction mixture was allowed to warm to room temperature and stirred overnight, then diluted with ether and filtered through sintered funnel. The filtrate was concentrated and the residue was purified by silica column chromatography (gradient hexane-ethyl acetate 6:1→2:1). The desired product 6a was obtained in 64% yield (1.37 g, 3.07 mmol).

Workup

  1. filtrationfiltered through sintered funnel
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified by silica column chromatography (gradient hexane-ethyl acetate 6:1→2:1)

Sources & evidence

ORD record
ord-e473e92ae9fb4616837a80f4d50f6759
Source dataset
uspto-grants-2010_09
Patent number
US07803960B2

Reaction notes

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