Carbon tetrabromide → 1-(3-Bromoprop-1-yn-1-yl)-4-fluorobenzene

HRID 334552Notes

Reaction equation

HRID 334552 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10]O)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:32]>C(Cl)Cl>[Br:32][CH2:10][C:9]#[C:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 27826983-(4-Fluorophenyl)prop-2-yn-1-ol

Product 1

HCID 105605241-(3-Bromoprop-1-yn-1-yl)-4-fluorobenzeneYield 99.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3-(4-fluorophenyl)prop-2-yn-1-ol (1 g, 6.80 mmol) in DCM (13.6 mL) under N2 was cooled in a ice bath at 0° C. 2.70 g (8.2 mmol, loading 3 mmol/g) of triphenylphosphine polymer supported was then added followed by 2.70 g (8.2 mmol) of carbon tetrabromide. The reaction mixture was stirred 15 min at 0° C. and warmed to room temperature for 90 min. After filtration through celite, the solvent was evaporated under reduce pressure. The crude product was purified by flash chromatography (prepacked 25 g silicagel column, DCM 100% as eluent) to afford 1.44 g of 1-(3-bromoprop-1-ynyl)-4-fluorobenzene as a yellow oil (Yield: 99%).

Workup

  1. temperaturewarmed to room temperature for 90 min
  2. filtrationAfter filtration through celite
  3. customthe solvent was evaporated
  4. customThe crude product was purified by flash chromatography (prepacked 25 g silicagel column, DCM 100% as eluent)

Sources & evidence

ORD record
ord-be071408f1204465bad74f652f817451
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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