Imidazole → Phenol, 4-(4-bromobutyl)-

HRID 993444Notes

Reaction equation

HRID 993444 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.[OH:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][CH2:31][CH2:32]O)=[CH:25][CH:24]=1.N1C=CN=C1>C(Cl)Cl>[OH:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][CH2:31][CH2:32][Br:20])=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 11776TriphenylphosphineHCID 24408BromineHCID 133925134-(4-Hydroxybutyl)phenol

Product 1

HCID 11128076Phenol, 4-(4-bromobutyl)-Yield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of triphenylphosphine (144.1 mmole, 37.80 g) in methylene chloride (556 ml) was treated with bromine (144.1 mmole, 23.03 g) until a pale yellow color persisted. After stirring approximately 15 minutes, a solution of 4-(4-hydroxyphenyl)butanol (96.1 mmole, 15.97 g) and imidazole (192.2 mmole, 13.08 g) in methylene chloride (355 ml) was added over a 15 minute period. Approximately 4 hours later, the reaction suspension was filtered and the filtrate was reduced in volume. To the reduced filtrate was added silica gel and the suspension was reduced to dryness. This material was filtered and the first six fractions were eluted with 10% ethyl acetate:hexane. Fractions 7 through 12 were eluted with 20% ethyl acetate:hexane. Fractions 7 through 10 were combined, reduced in volume, dried over sodium sulfate, filtered and concentrated in vacuo to afford 19.32 g (88%) of the title compound as an oil.

Workup

  1. filtrationApproximately 4 hours later, the reaction suspension was filtered
  2. additionTo the reduced filtrate was added silica gel
  3. filtrationThis material was filtered
  4. washthe first six fractions were eluted with 10% ethyl acetate
  5. washFractions 7 through 12 were eluted with 20% ethyl acetate
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-82ded934315e4ef9a19b1089bc67347d
Source dataset
uspto-grants-2002_10
Patent number
US06472387B1

Reaction notes

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