Hydrogen Bromide → HCID 14496389, compound

HRID 2372663Notes

Reaction equation

HRID 2372663 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:17][CH:16]=3)=[N:13][CH:14]=2)=[CH:5][CH:4]=1.Br>C(O)(=O)C>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[N:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:17][CH:16]=3)=[N:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 14496388HCID 14496388, compound

Product 1

HCID 14496389HCID 14496389, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 5-(4-methoxyphenyl)-2-(4-nonylphenyl)-pyrimidine (60 g), hydrobromic acid (240 g) and acetic acid (1 l ) was refluxed for 40 hours, followed by distilling off most part of the acetic acid, pouring the residue into 2N-NaOH aqueous solution and recrystallizing the deposited crystals from ethyl acetate to obtain 5-(4-hydroxyphenyl)-2-(4-nonylphenyl)pyrimidine (32.6 g). This product had a C-SA point of 98.4° C. and a SA-I point of 138.6° C.

Workup

  1. temperaturewas refluxed for 40 hours
  2. distillationby distilling off most part of the acetic acid
  3. additionpouring the residue into 2N-NaOH aqueous solution
  4. customrecrystallizing the deposited crystals from ethyl acetate

Sources & evidence

ORD record
ord-dbb4a666695a48fea7e6e1002105e519
Source dataset
uspto-grants-1992_03
Patent number
US05100578

Reaction notes

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