Carbon tetrabromide → HCID 22672715, compound

HRID 726102Notes

Reaction equation

HRID 726102 reaction equation
[CH2:1]([N:5]([CH3:17])[C:6](=[O:16])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]#[C:13][CH2:14]O)[CH2:2][CH2:3][CH3:4].C(Br)(Br)(Br)[Br:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:19][CH2:14][C:13]#[C:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH3:17])=[O:16]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22672768HCID 22672768, compound

Product 1

HCID 22672715HCID 22672715, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1.65 g of the product of Step B in 16.5 ml of methylene chloride cooled to -5° C. there were added 2.85 g of carbon tetrabromide and 2.25 g of triphenylphosphine. The reaction solution was stirred for 30 minutes at 0° C. and chromatographed on silica (eluant: methylene chloride-ethyl acetate 90-10) to obtain 1.82 g of the desired product.

Workup

  1. customchromatographed on silica (eluant: methylene chloride-ethyl acetate 90-10)

Sources & evidence

ORD record
ord-25549fd5d3114cb5a902dd433b846676
Source dataset
uspto-grants-1998_01
Patent number
US05707982

Reaction notes

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