Pyridine → Benzeneacetyl chloride, 4-bromo-

HRID 1446674Notes

Reaction equation

HRID 1446674 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.N1C=CC=CC=1.C(Cl)(=O)C([Cl:21])=O.CN(C=O)C>CCOCC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([Cl:21])=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 74654Benzeneacetic acid, 4-bromo-

Product 1

HCID 181552Benzeneacetyl chloride, 4-bromo-Yield 99.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Dissolve 4-bromophenylacetic acid (25.39; 118.07 mmol) in ether (200 mL). Add anhydrous pyridine (1 mL) and cool the reaction to 0° C., then add oxalyl chloride (18.44 g, 12.86 mL, 145.32 mmol). After 15 minutes, allow the reaction to come to ambient temperature. At 1.5 hours, add DMF (0.4 mL) and stir for an additional hour. Concentrate to a thick amber oil. Dilute with dichloromethane (118 mL) to provide a 1 N stock solution of (4-bromo-phenyl)-acetyl chloride (118 mmol).

Workup

  1. customthe reaction to 0° C.
  2. customthe reaction
  3. customto come to ambient temperature
  4. waitAt 1.5 hours
  5. concentrationConcentrate to a thick amber oil
  6. additionDilute with dichloromethane (118 mL)

Sources & evidence

ORD record
ord-ab927b2774c043ccaa727185768f948f
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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