Bromine → HCID 23314490, compound

HRID 745137Notes

Reaction equation

HRID 745137 reaction equation
[C:1]([C:4]1[C:5]([O:15][CH3:16])=[CH:6][C:7]([O:13][CH3:14])=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10])(=[O:3])[CH3:2].[Br:17]Br>O1CCOCC1>[Br:17][CH2:2][C:1]([C:4]1[C:5]([O:15][CH3:16])=[CH:6][C:7]([O:13][CH3:14])=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10])=[O:3]

Participants

4

Reactant 2

HCID 24408Bromine2×HCID 3298125-Acetyl-2,4-dimethoxybenzoic acid

Product 1

HCID 23314490HCID 23314490, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5-Acetyl-2,4-dimethoxybenzoic acid (Ber. 41, 1607, 1908) (21.1 g, 0.094 mole) was stirred in dioxane (200 ml.) at room temperature and bromine (5 ml., ca 0.1 mole) was added dropwise. The bromine colour gradually disappeared over 30 minutes and the mixture was then gently warmed in a steambath for 30 minutes, cooled and the dioxane removed in vacuo. The solid product was treated with boiling ethyl acetate, filtered hot and the filtrate evaporated to give 5-bromoacetyl-2,4-dimethoxybenzoic acid, m.p. 236° C.

Workup

  1. temperaturethe mixture was then gently warmed in a steambath for 30 minutes
  2. temperaturecooled
  3. customthe dioxane removed in vacuo
  4. additionThe solid product was treated with boiling ethyl acetate
  5. filtrationfiltered hot
  6. customthe filtrate evaporated

Sources & evidence

ORD record
ord-92366e5aef104c3a90a0a732fa753227
Source dataset
uspto-grants-1986_07
Patent number
USRE032196

Reaction notes

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