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

HRID 1586076Notes

Reaction equation

HRID 1586076 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 5 mins and then at room temperature for 1 hr. The reaction mixture was then evaporated under reduced pressure and the crude product was chromatographed on silica-gel (25 g). Elution with 50% 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, OC3) 4.68 (s, 2H, CH2Br).

Workup

  1. waitat room temperature for 1 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 50% ether-hexane

Sources & evidence

ORD record
ord-7a664d584659413aa34a5559c2bf6e19
Source dataset
uspto-grants-1999_08
Patent number
US05942522

Reaction notes

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