Triphenylphosphine → 3-[4-(2-Methyltetrazol-5-yl)-2,6-dimethylphenoxy]-propylbromide

HRID 863595

Reaction equation

HRID 863595 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][Br:5].[CH3:6][N:7]1[N:11]=[N:10][C:9]([C:12]2[CH:17]=[C:16]([CH3:18])[C:15](O)=[C:14]([CH3:20])[CH:13]=2)=[N:8]1.CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O.CCOCC>[CH3:6][N:7]1[N:11]=[N:10][C:9]([C:12]2[CH:13]=[C:14]([CH3:20])[C:15]([O:1][CH2:2][CH2:3][CH2:4][Br:5])=[C:16]([CH3:18])[CH:17]=2)=[N:8]1

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 123083-Bromo-1-propanolHCID 148372Win 58768HCID 5462977Diethyl azodicarboxylate

Product 1

HCID 153915233-[4-(2-Methyltetrazol-5-yl)-2,6-dimethylphenoxy]-propylbromideYield 82%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (3-hydroxypropyl)-bromide (2.17 ml, 24 mmol), 4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenol (5.1 g, 25 mmol), and DEAD (4.18 g, 24 mmol) was dissolved in 50 ml of THF at 0° C. To the above solution was added dropwise triphenylphosphine (6.3 g, 24 mmol) at 0° C. and the mixture was allowed to stir at 0° C. for 0.5 h. The mixture was diluted with 500 ml of water and 100 ml of ether, and the aqueous layere was extracted with ether (2×400 ml). The combined organic layer was dried over sodium sulfate, and concentrated in vacuo. The residue was dissolved in 800 ml of ether, and the organic layer was washed with 10% NaOH solution (3×50 ml), dried over sodium sulfate, and concentrated in vacuo. The residue was purified by silica column chromatography (7 cm column, ethyl acetate/hexane, 1/5) followed by recrystallization from methylene chloride/hexane to afford 6.4 g (82%) of 3-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]-propylbromide, as a light yellow oil.

Workup

  1. extractionthe aqueous layere was extracted with ether (2×400 ml)
  2. dry with materialThe combined organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in 800 ml of ether
  5. washthe organic layer was washed with 10% NaOH solution (3×50 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica column chromatography (7 cm column, ethyl acetate/hexane, 1/5)
  9. customfollowed by recrystallization from methylene chloride/hexane

Sources & evidence

ORD record
ord-792e706ecee04535a5e151d198656c3c
Source dataset
uspto-grants-1998_02
Patent number
US05721261

Linked notes

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