Hydrogen Bromide → 106808-99-5

HRID 35149Notes

Reaction equation

HRID 35149 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:11][N:10]=2)=[CH:5][C:4]=1[F:23].Br>C(O)(=O)C>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:11][N:10]=2)=[CH:5][C:4]=1[F:23]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 19850585HCID 19850585, compound

Product 1

HCID 135689415106808-99-5Yield 101.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

This 2-(p-methoxy-m-fluorophenyl)-5-octylpyrimidine (50 g) was heated for substitution together with glacial acetic acid (500 ml) and hydrobromic acid (47%) (170 g) for 72 hours, followed by distilling off acetic acid and hydrobromic acid under reduced pressure, adding aqueous NaOH and toluene, extracting the objective substance into the toluene layer and then distilling off toluene to obtain 2-(p-hydroxy-m-fluorophenyl)-5-octylpyrimidine ((i); Y=F, m=8) (48.5 g). This product was used in the next stage without its purification.

Workup

  1. distillationby distilling off acetic acid and hydrobromic acid under reduced pressure
  2. additionadding aqueous NaOH and toluene
  3. extractionextracting the objective substance into the toluene layer
  4. distillationdistilling off toluene

Sources & evidence

ORD record
ord-2865e093fcc540aebcf8dcf591ecdaff
Source dataset
uspto-grants-1988_08
Patent number
US04765924

Reaction notes

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