Carbon tetrabromide → 1-hexyl-3-bromomethyl-4-methoxy-6-methyl-2(1H)-quinolinone

HRID 36050Notes

Reaction equation

HRID 36050 reaction equation
[CH2:1]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=2)[C:10]([O:18][CH3:19])=[C:9]([CH2:20]O)[C:8]1=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(Br)(Br)(Br)[Br:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH2:1]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=2)[C:10]([O:18][CH3:19])=[C:9]([CH2:20][Br:24])[C:8]1=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 97964601-hexyl-3-hydroxymethyl-4-methoxy-6-methyl-2(1H)-quinolinone

Product 1

HCID 152333491-hexyl-3-bromomethyl-4-methoxy-6-methyl-2(1H)-quinolinone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1 -hexyl-3-hydroxymethyl-4-methoxy-6-methyl-2(1H)-quinolinone (Example 12, 0.6 g) in methylene chloride (12 ml) containing carbon tetrabromide (1 g) was treated with triphenylphosphine (0.87 g) and stirred at ice bath temperature for 5mins and then at room temperature for hr. The reaction mixture was then evaporated under reduced pressure and the crude product was chromatographed on silica-gel (25 g). Elution with ether-hexane gave 1-hexyl-3-bromomethyl-4-methoxy-6-methyl-2(1H)-quinolinone as a white crystralline solid. That the expected product was obtained was confirmed by the spectral data: MS: m/e 365,367 (M+); NMR (CDCl3): δ4.12 (s, 3H, OCH3) 4.68 (s, 2H, CH2Br).

Workup

  1. waitat room temperature for hr
  2. customThe reaction mixture was then evaporated under reduced pressure
  3. customthe crude product was chromatographed on silica-gel (25 g)
  4. washElution with ether-hexane

Sources & evidence

ORD record
ord-e35f842b46234311aded068b70c38c4b
Source dataset
uspto-grants-1995_05
Patent number
US05412104

Reaction notes

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