Carbon tetrabromide → HCID 10384209, compound

HRID 1028488Notes

Reaction equation

HRID 1028488 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([CH:13](O)[C:14]([O:16][CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(Br)(Br)(Br)[Br:22].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([CH:13]([Br:22])[C:14]([O:16][CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

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-8d49097bfa234be58f77262e47a3ba09
Source dataset
uspto-grants-2014_05
Patent number
US08735435B2

Reaction notes

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