Carbon tetrabromide → HCID 88531024, compound

HRID 1916877Notes

Reaction equation

HRID 1916877 reaction equation
[F:1][C:2]([F:33])([F:32])[O:3][C:4]1[CH:31]=[CH:30][C:7]([CH2:8][N:9]([C:16]2[N:17]=[C:18]3[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][N:19]3[C:28]=2[CH3:29])[S:10]([CH2:13][CH2:14]O)(=[O:12])=[O:11])=[CH:6][CH:5]=1.C(Br)(Br)(Br)[Br:35].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[F:1][C:2]([F:33])([F:32])[O:3][C:4]1[CH:31]=[CH:30][C:7]([CH2:8][N:9]([C:16]2[N:17]=[C:18]3[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][N:19]3[C:28]=2[CH3:29])[S:10]([CH2:13][CH2:14][Br:35])(=[O:12])=[O:11])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 88531095HCID 88531095, compound

Product 1

HCID 88531024HCID 88531024, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 17-G (0.031 g, 0.062 mmol) and carbon tetrabromide (0.025 g, 0.075 mmol) in methylene chloride (1.5 mL) at 0° C. was added triphenylphosphine (0.020 g, 0.075 mmol). The ice bath was removed and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and the resulting residue was purified by flash column chromatography, eluting with a hexanes-EtOAc gradient to give compound 17-H as a white solid (0.010 g, 29%); MS m/z (M+H+) 560.

Workup

  1. customThe ice bath was removed
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe resulting residue was purified by flash column chromatography
  4. washeluting with a hexanes-EtOAc gradient

Sources & evidence

ORD record
ord-24022427257a4bd69ccbaed2267d6ca2
Source dataset
uspto-grants-2013_12
Patent number
US08618150B2

Reaction notes

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