Hydrochloric Acid → 5-(2-Bromophenyl)-4-pentynoic acid

HRID 1722333Notes

Reaction equation

HRID 1722333 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][CH2:3][C:4]#[CH:5].[Br:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1I.Cl>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd].[Cu]I.C(NCC)C>[Br:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:5]#[C:4][CH2:3][CH2:2][C:1]([OH:7])=[O:6]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 114151-Bromo-2-iodobenzeneHCID 224644-Pentynoic acid

Product 1

HCID 147984675-(2-Bromophenyl)-4-pentynoic acid

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8021DiethylamineSolvent

Procedure

To 10 ml of diethylamine was added with stirring 0.5 g (5.1 mmol) of 4-pentynoic acid, 1.4g (5 mmol) of 1-bromo-2-iodobenzene, and 60mg (0.05 mmol) of tetrakis(triphenylphosphine)palladium(O) The slurry was degassed with argon and 0.19g (1.0 mmol) of CuI was added. The reaction mixture was stirred for 2 hr. at room temperature and then poured into approximately 100ml of a 10% HCl solution. The resulting precipitate was filtered, washed with water and dried. The solid was taken up in hot CHCl3 and filtered to remove insoluble salts. After evaporation of the solvent, the resulting orange solid was recrystallized from a chloroform-hexane mixture to produce a tan solid, m.p. 87-91°C.

Workup

  1. additionwas added
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. customdried
  5. filtrationfiltered
  6. customto remove insoluble salts
  7. customAfter evaporation of the solvent
  8. customthe resulting orange solid was recrystallized from a chloroform-hexane mixture
  9. customto produce a tan solid, m.p. 87-91°C.

Sources & evidence

ORD record
ord-faa30264305d4ebdb1c8ba56d797c0bf
Source dataset
uspto-grants-1989_08
Patent number
US04855324

Reaction notes

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