Carbon tetrabromide → HCID 10384209, compound

HRID 1994459Notes

Reaction equation

HRID 1994459 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH:4]([C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([C:16]([F:19])([F:18])[F:17])[CH:7]=1)O.C(Br)(Br)(Br)[Br:22].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:20])[CH:4]([C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([C:16]([F:19])([F:18])[F:17])[CH:7]=1)[Br:22]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 81654350HCID 81654350, compound

Product 1

HCID 10384209HCID 10384209, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methyl[3,5-bis(trifluoromethyl)phenyl](hydroxy)acetate (300 mg, 0.993 mmol) was dissolved in CH2Cl2 (10 mL). The solution was cooled to 0° C. and CBr4 (659 mg, 1.986 mmol) was added followed by PPh3 (521 mg, 1.986 mmol). After 1 hour, the reaction was warmed to room temperature and stirred at room temperature for 1 hour. The reaction was filtered through a short plug of silica gel with CH2Cl2. The filtrate was concentrated and the residue was purified by flash chromatography with 5% EtOAc/hexanes to afford methyl[3,5-bis(trifluoromethyl)phenyl](bromo)acetate. Rf=0.24 (5% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) δ 8.02 (s, 2H), 7.87 (s, 1H), 5.41 (s, 1H), 3.83 (s, 3H).

Workup

  1. temperaturethe reaction was warmed to room temperature
  2. filtrationThe reaction was filtered through a short plug of silica gel with CH2Cl2
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by flash chromatography with 5% EtOAc/hexanes

Sources & evidence

ORD record
ord-37ff4daa8f3b4136b72d390477ba6024
Source dataset
uspto-grants-2010_01
Patent number
US07652049B2

Reaction notes

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