Formaldehyde → 2,4-Dibromo-6-[(tert-butylamino)methyl]phenol

HRID 1973174Notes

Reaction equation

HRID 1973174 reaction equation
[CH2:1]=O.[C:3]([NH2:7])([CH3:6])([CH3:5])[CH3:4].[Br:8][C:9]1[CH:14]=[C:13]([Br:15])[CH:12]=[CH:11][C:10]=1[OH:16]>O1CCOCC1>[OH:16][C:10]1[C:9]([Br:8])=[CH:14][C:13]([Br:15])=[CH:12][C:11]=1[CH2:1][NH:7][C:3]([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6385Tert-ButylamineHCID 120052,4-Dibromophenol

Product 1

HCID 5476212,4-Dibromo-6-[(tert-butylamino)methyl]phenol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent3×

Conditions

Temperature
15 °C

Procedure

A mixture of 95 ml of 35% formaldehyde solution and 100 ml of dioxane is dropped into a solution of 80 g of tertiary butylamine in 350 ml of dioxane, cooled to 15° C, with stirring. The mixture is allowed to stand over night, then heated to 80° C. In the course of 4 hours a solution of 252 g of 2,4-dibromophenol in 250 ml of dioxane is dropped thereto, precipitating thereby the main charge of the reaction product. 1 hour after completion of this addition it is cooled, the precipitate is sucked off, washed with ethanol on the filter and dried. By concentrating the dioxane-mother liquor and the alcoholic washing liquid further material is obtained. Remaining reaction product precipitates from the dioxane concentrate in form of the hydrochloride by heating with alcoholic HCl. The hydrochloride is converted in H2O/CHCl3 in the free base with HaHCO3. Total yield = 268 g (79,5% of the theory). Recrystallization from acetic ester yields the N-(2-hydroxy-3,5-dibromobenzyl)-tert.butylamine in form of colorless felted needles, melting at 173° - 175° C.

Workup

  1. waitto stand over night
  2. temperatureheated to 80° C
  3. customprecipitating
  4. additionthe main charge of the reaction product
  5. addition1 hour after completion of this addition it
  6. temperatureis cooled
  7. washwashed with ethanol on the
  8. filtrationfilter
  9. customdried
  10. concentrationBy concentrating the dioxane-mother liquor
  11. washthe alcoholic washing liquid further material
  12. customis obtained
  13. customRemaining reaction product precipitates from the dioxane
  14. concentrationconcentrate in form of the hydrochloride
  15. temperatureby heating with alcoholic HCl
  16. customRecrystallization from acetic ester

Sources & evidence

ORD record
ord-8c15e802fcb24add97002a2e54a98777
Source dataset
uspto-grants-1976_12
Patent number
US03996278

Reaction notes

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