Water → 2-Bromo-4-(5-decyl-2-pyrimidinyl)phenol

HRID 1707910Notes

Reaction equation

HRID 1707910 reaction equation
[CH2:1]([C:11]1[CH:12]=[N:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)=[N:15][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[Br:24]Br.O>ClCCl>[Br:24][C:19]1[CH:18]=[C:17]([C:14]2[N:15]=[CH:16][C:11]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])=[CH:12][N:13]=2)[CH:22]=[CH:21][C:20]=1[OH:23]

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 135585902Phenol, 4-(5-decyl-2-pyrimidinyl)-

Product 1

HCID 1356242352-Bromo-4-(5-decyl-2-pyrimidinyl)phenolYield 76.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5 g of 4-(5-decyl-2-pyrimidinyl)phenol in 50 ml of dichloromethane was treated at 0° C. while gassing with argon with a solution of 2.6 g of bromine in 50 ml of dichloromethane. The reaction mixture was stirred for a further 2 hours and then treated with water. The organic phase was separated and the aqueous phase was back-extracted three times with 50 ml of dichloromethane each time. The combined organic phases were washed with water, sodium hydrogen carbonate solution and again with water, dried over magnesium sulfate0 filtered and subsequently concentrated. The residue was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 4;1). Recrystallization from hexane gave 4.8 g of 2-bromo-4-(5-decyl-2-pyrimidinyl)phenol.

Workup

  1. customThe organic phase was separated
  2. extractionthe aqueous phase was back-extracted three times with 50 ml of dichloromethane each time
  3. washThe combined organic phases were washed with water, sodium hydrogen carbonate solution and again with water
  4. dry with materialdried over magnesium sulfate0
  5. filtrationfiltered
  6. concentrationsubsequently concentrated
  7. customThe residue was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 4;1)
  8. customRecrystallization from hexane

Sources & evidence

ORD record
ord-177d7e0f8a124f3596f26a483f4ac4cc
Source dataset
uspto-grants-1994_10
Patent number
US05356563

Reaction notes

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