Dichloromethane → 173019-82-4

HRID 2414575Notes

Reaction equation

HRID 2414575 reaction equation
[Br:1][CH2:2][C:3]#[C:4][C:5]1[CH:10]=[CH:9][C:8](O)=[CH:7][CH:6]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.BrBr.[Cl:33]CCl>>[Br:1][CH2:2][C:3]#[C:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:33])=[CH:7][CH:6]=1

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 11776TriphenylphosphineHCID 24408BromineHCID 226448974-(3-Bromoprop-1-YN-1-YL)phenol

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-7b2a6725032e42e49c5592a95d28a21a
Source dataset
uspto-grants-2004_11
Patent number
US06812227B2

Reaction notes

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