Triphenylphosphine → Ethyl4-(4-bromomethyl-3-methyl-phenylethynyl)-benzoate

HRID 2185356Notes

Reaction equation

HRID 2185356 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:11]2[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=2)=[CH:5][C:4]=1[CH3:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:42]N1C(=O)CCC1=O>C(Cl)Cl>[Br:42][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:11]2[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=2)=[CH:5][C:4]=1[CH3:22]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 22568788HCID 22568788, compound2×

Product 1

HCID 22568891Ethyl4-(4-bromomethyl-3-methyl-phenylethynyl)-benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 4-(4-hydroxymethyl-3-methyl-phenylethynyl)-benzoate (Compound 117, 130.0 mg, 0.44 mmol) and triphenylphosphine (150.0 mg, 0.57 mmol) in 5 mL CH2Cl2 was cooled to 0° C. and N-bromosuccinimide (101.0 mg, 0.57 mmol) was added in 5 portions over 20 minutes. The solution was warmed to 25 IC and stirred for 17 hours. The reaction was quenched by the addition of dilute aqueous NaHCO3. The resulting mixture was extracted with Et2O and the combined organic layers were washed with H2O and saturated aqueous Nacl before being dried (Na2SO4) and concentrated under reduced pressure. The title compound, 120.0 mg (76%), was isolated by column chromatography (2-5% EtOAc-hexanes) as a colorless solid.

Workup

  1. temperatureThe solution was warmed to 25 IC
  2. customThe reaction was quenched by the addition of dilute aqueous NaHCO3
  3. extractionThe resulting mixture was extracted with Et2O
  4. washthe combined organic layers were washed with H2O and saturated aqueous Nacl
  5. dry with materialbefore being dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d667709c88304c34882d4dd9e46d25ba
Source dataset
uspto-grants-2002_06
Patent number
US06399774B1

Reaction notes

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