Phenol → 173019-82-4

HRID 1976411Notes

Reaction equation

HRID 1976411 reaction equation
[C:1]1(O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P([C:21]2[CH:26]=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:27]Br.Cl[CH2:30][Cl:31]>>[Br:27][CH2:2][C:3]#[C:4][C:5]1[CH:6]=[CH:1][C:30]([Cl:31])=[CH:21][CH:26]=1

Participants

5

Reactant 4

HCID 996PhenolHCID 6344Dichloromethane2×HCID 11776TriphenylphosphineHCID 24408Bromine

Product 1

HCID 10513607173019-82-4Yield 80%

Conditions

Temperature
0 °C

Procedure

To a solution of 4-3-bromo-prop-1-ynyl)-phenol (5.0 g, 30.12 mmol) dissolved in dichloromethane, 8.3 g (31.63 mmol, 1.05 eq) of triphenylphosphine was added and the solution was cooled to 0° C. Bromine (1.55 mL, 30.12 mmol, 1.0 eq) was added dropwise and the reaction was warmed to room temperature. The reaction was then diluted with dichloromethane, washed with sodium hydrosulfite pentahydrate, washed with brine, dried over MgSO4 and concentrated. The residue was purified via flash chromatography using 4:1 hexane:ethyl acetate to afford 5.56 g (80%) of 1-(3-bromo-prop-1-ynyl)-4-chloro-benzene as an amber oil. Electrospray Mass Spec 280.4 (M+H)+

Workup

  1. temperaturethe reaction was warmed to room temperature
  2. washwashed with sodium hydrosulfite pentahydrate
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified via flash chromatography

Sources & evidence

ORD record
ord-c876602986594fd09f84ba16dda070de
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

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