Dichloromethane → HCID 20827109, compound

HRID 401672Notes

Reaction equation

HRID 401672 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[Cl-].[F:13][C:14]([F:24])([F:23])[C:15]1[CH:22]=[CH:21][C:18]([CH2:19][Zn+])=[CH:17][CH:16]=1.C(Cl)Cl>C1COCC1>[F:13][C:14]([F:23])([F:24])[C:15]1[CH:22]=[CH:21][C:18]([CH2:19][C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 12081Methyl 4-bromobenzoateHCID 178506169HCID 178506169, compound

Product 1

HCID 20827109HCID 20827109, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Argon was bubbled through a mixture of methyl 4-bromobenzoate 42a (9.3 mmol, 2.0 g), 2 mL of THF, and 4-trifluoromethylbenzylzinc chloride (0.5 M in THF, 46.5 mmol, 93 mL) for 5 min. Pd(dffp)Cl2.CH2Cl2 (0.5 mol, 409 mg) was added and the reaction tube was capped and heated at 70° C. for 16 h. The mixture was cooled and filtered through Celite. Water was added to the filtrate and the resulting solid was filtered off. The organic solution was dried over MgSO4 and concentrated. The crude product was purified by flash chromatography (silica gel, 0-10% EtOAc in heptane) to give 1.5 g (55%) of methyl 4-(4-(trifluoromethyl)benzyl)benzoate, 42b.

Workup

  1. customthe reaction tube was capped
  2. temperatureThe mixture was cooled
  3. filtrationfiltered through Celite
  4. additionWater was added to the filtrate
  5. filtrationthe resulting solid was filtered off
  6. dry with materialThe organic solution was dried over MgSO4
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography (silica gel, 0-10% EtOAc in heptane)

Sources & evidence

ORD record
ord-4c9a2df8051c40faa9365b4f494e75d7
Source dataset
uspto-grants-2014_06
Patent number
US08741887B2

Reaction notes

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