Carbon tetrabromide → HCID 19025816, compound

HRID 1033243Notes

Reaction equation

HRID 1033243 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:14])[CH2:9][CH2:10][CH2:11][CH2:12][Br:13].C(Br)(Br)(Br)[Br:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:16][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:14])[CH2:9][CH2:10][CH2:11][CH2:12][Br:13]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 19025805HCID 19025805, compound

Product 1

HCID 19025816HCID 19025816, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Part A. A solution of N-(5-hydroxypentyl)-5-bromopentanamide (4.07 g, 15.3 mmol) and carbon tetrabromide (7.61 g, 22.9 mmol) in methylene chloride (75 mL) was cooled to 0° C., and treated with a solution of triphenylphosphine (6.02 g, 22.9 mmol) in methylene chloride (30 mL) dropwise. After stirring for 12 hours, the reaction mixture was evaporated, and the residual oil was separated by flash chromatography (1:1 ethyl acetate-hexane) to afford the oily product, N-(5-bromopentyl)-5-bromopentanamide (1.69 g, 5.14 mmol, 34%). 1H NMR (CDCl3): 5.96 (1H, br s); 3.40 (4H, t, J=6.6 Hz); 3.24 (2H, q, J=6.2 Hz); 2.20 (2H, t, J=7.0 Hz); 1.94-1.74 (6H, m); 1.58-1.42 (4H, m).

Workup

  1. customthe reaction mixture was evaporated
  2. customthe residual oil was separated by flash chromatography (1:1 ethyl acetate-hexane)

Sources & evidence

ORD record
ord-da771a0730154e1cb87f770ecec5db0e
Source dataset
uspto-grants-1994_05
Patent number
US05310748

Reaction notes

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