Benzene, 1-bromo-3-(trifluoromethyl)- → HCID 178447605, compound

HRID 920862Notes

Reaction equation

HRID 920862 reaction equation
[C:1]([O-:7])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Zn+2:8].C([O-])(=O)C(C)(C)C.Br[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=1.[Mg]>>[C:1]([O-:7])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[F:24][C:23]([F:26])([F:25])[C:19]1[CH:18]=[C:17]([Zn+:8])[CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 9817Benzene, 1-bromo-3-(trifluoromethyl)-HCID 5462224MagnesiumHCID 19435776Zinc pivalate

Product 1

HCID 178447605HCID 178447605, compoundYield 84%

Conditions

Temperature
25 °C

Procedure

2LiCl (2a prepared above; 2.64 g, 7.50 mmol) is placed in a 25 mL Schlenk-flask, dried for 5 min at 400° C. (heat gun) in high vacuum and then dissolved in dry THF (10.0 mL). 1-Bromo-3-(trifluoromethyl)benzene (3d; 1.13 g, 5.00 mmol) and magnesium-turnings (304 mg, 12.5 mmol) are added and the mixture was stirred for 2 h at 25° C. The solution is cannulated to a dry and argon-flushed 50 mL Schlenk-tube via syringe filter and the solvent is removed in vacuo. 3-(Trifluoromethyl)phenylzinc pivalate (1d) is obtained as a grey solid (3.72 g).

Workup

  1. customis placed in a 25 mL Schlenk-flask
  2. customdried for 5 min at 400° C.
  3. temperature(heat gun) in high vacuum
  4. dissolutiondissolved in dry THF (10.0 mL)
  5. customa dry
  6. customargon-flushed 50 mL Schlenk-tube via syringe
  7. filtrationfilter
  8. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-69b00f86700e444bb04c9aa7824605e0
Source dataset
uspto-grants-2016_03
Patent number
US09273070B2

Reaction notes

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