Bromine → HCID 14520030, compound

HRID 1607770Notes

Reaction equation

HRID 1607770 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11]([CH:15]=[O:16])=[C:10]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:9]=[CH:8]2>C(O)(=O)C>[Br:1][C:6]1[C:5]([O:4][CH3:3])=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][C:10]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[C:11]2[CH:15]=[O:16]

Participants

4

Reactant 2

HCID 24408BromineHCID 14520029HCID 14520029, compound

Product 1

HCID 14520030HCID 14520030, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Bromine (3.22 mL, 62.5 mmol) was dissolved in 60 mL of glacial acetic acid and added, over a 20 minute period, to a solution of 6-methoxy-2-(phenylmethoxy)-1-naphthalenecarboxaldehyde (17.4 g, 59.5 mmol, described in Example 5) in 270 mL of glacial acetic acid at 45° C. The resulting suspension was allowed to cool for 1 hour, then the precipitate was collected by filtration and washed thoroughly with absolute ethanol. The solid was suspended in 170 mL of toluene and concentrated by distillation at ambient pressure until about 30 mL remained then allowed to stand at room temperature overnight. The precipitate which formed upon cooling was collected by filtration and washed with hexane to give 18.14 g of the title compound as a yellow powder, m.p. 214°-220° C.

Workup

  1. temperatureto cool for 1 hour
  2. filtrationthe precipitate was collected by filtration
  3. washwashed thoroughly with absolute ethanol
  4. concentrationconcentrated by distillation at ambient pressure until about 30 mL
  5. customThe precipitate which formed
  6. temperatureupon cooling
  7. filtrationwas collected by filtration
  8. washwashed with hexane

Sources & evidence

ORD record
ord-cc239270be0b41688c20d1a981eb92fd
Source dataset
uspto-grants-1989_09
Patent number
US04866197

Reaction notes

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