Carbon tetrabromide → HCID 19385599, compound

HRID 2255592Notes

Reaction equation

HRID 2255592 reaction equation
[CH2:1]([O:3][C:4]1[CH:21]=[C:20]([CH2:22]O)[CH:19]=[CH:18][C:5]=1[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH3:2].C(Br)(Br)(Br)[Br:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:25][CH2:22][C:20]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH2:13][C:14]([O:16][CH3:17])=[O:15])=[C:4]([O:3][CH2:1][CH3:2])[CH:21]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 19385715HCID 19385715, compound

Product 1

HCID 19385599HCID 19385599, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred and cooled (0° C.) solution of 1.15 g (3.64 mmol) of the product of Step B dissolved in 18 mL of CH2Cl2 was added 1.51 g (4.55 mmol) of carbon tetrabromide and 1.19 g (4.55 mmol) of triphenylphosphine. After the addition the reaction mixture was stirred 30 minutes and allowed to warm to room temperature. The mixture was then evaporated in vacuo and purified on a silica gel flash chromatography column eluted with 15% ethyl acetate/hexane to afford 1.21 g (88%) of the title compound.

Workup

  1. additionAfter the addition the reaction mixture
  2. stirringwas stirred 30 minutes
  3. customThe mixture was then evaporated in vacuo
  4. custompurified on a silica gel flash chromatography column
  5. washeluted with 15% ethyl acetate/hexane

Sources & evidence

ORD record
ord-3f70a320623f4b27aa04101289c5ceb0
Source dataset
uspto-grants-1993_08
Patent number
US05240938

Reaction notes

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