Dichloromethane → 173019-82-4

HRID 2084868Notes

Reaction equation

HRID 2084868 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-46b0059bf98547daa48be40891d66b8a
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

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