Bromine → HCID 10192904, compound

HRID 1836795Notes

Reaction equation

HRID 1836795 reaction equation
[Br-:1].[K+].BrBr.[C:5]([O:8][C:9]1[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=[O:12])(=[O:7])[CH3:6]>O>[C:5]([O:8][C:9]1[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[C:13]([Br:1])[C:10]=1[CH:11]=[O:12])(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 24408BromineHCID 2517032-Acetoxy-3-methoxybenzaldehydeHCID 253877Potassium Bromide

Product 1

HCID 10192904HCID 10192904, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of potassium bromide (40 g) in H2O (250 mL) was added bromine (6.8 mL). To the dark red solution was added aldehyde 10 (20.2 g). The turbid orange solution was stirred overnight, filtered, rinsed with ethyl acetate, recrystallized from ethyl acetate/hexane to afford yellow crystals (22.4 g, 79%): m.p. 121.6-123.4° C., lit18 m.p. 119-120° C.; EIMS m/z 274 (M+, 81Br), 272 (M+, 79Br), 232, 230, 186, 184, 43; 1H NMR δ 10.26 (1H, s, CHO), 7.51 (1H, d, J=9.0 Hz, H4), 7.05 (1H, d, J=9.0 Hz H2, H4), 3.85 (3H, s, OCH3), 2.38 (3H, s, COCH3); 13C—NMR (75.5 MHZ) δ 190.38, 168.71, 151.78, 140.37, 131.41, 126.49, 117.69, 116.35, 56.40, 20.44. Anal. Calcd. For C10H9O4Br: C, 43.98; H, 3.32. Found: C, 44.46; H, 3.55.

Workup

  1. filtrationfiltered
  2. washrinsed with ethyl acetate
  3. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-432065092de1456f9baeace584818f96
Source dataset
uspto-grants-2004_08
Patent number
US06777578B2

Reaction notes

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