Toluene → 4-tert-Butylbenzotrifluoride

HRID 726139Notes

Reaction equation

HRID 726139 reaction equation
[C:1]1(C)C=CC=CC=1.C[Zn]C.[F:11][C:12]([F:24])([F:23])[C:13]1[CH:22]=[CH:21][C:16]([C:17](Cl)([CH3:19])[CH3:18])=[CH:15][CH:14]=1>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[F:11][C:12]([F:24])([F:23])[C:13]1[CH:22]=[CH:21][C:16]([C:17]([CH3:1])([CH3:19])[CH3:18])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 197097954-Trifluoromethyl-alpha,alpha-dimethylbenzyl chlorideHCID 178477796HCID 178477796, compound

Product 1

HCID 120705444-tert-Butylbenzotrifluoride

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-40 °C

Procedure

To a toluene solution of dimethylzinc (150 mL, 2.0M, 0.30 mol) at -78° C. is added a CH2Cl2 solution of titanium tetrachloride (150 mL, 1.0 M, 0.15 mol) and after stirring for 30 min 4-trifluoromethyl-α,α-dimethylbenzyl chloride (83.3 g, 0.373 mol) in CH2Cl2 (100 mL) is added dropwise over 20 min. After the addition is complete the reaction is allowed to warm to -40° C. over 1.5 h. After an additional 2 h at -40° C. the brown reaction mixture is carefully poured onto crushed ice, extracted with CH2 Cl2 (2×500 mL), the combined extracts dried over MgSO4 and concentrated to give 4-trifluoromethyl-t-butylbenzene; yield: 60.3 g (80%). Anal. Calcd. for C11H13F3 : C, 65.32; H, 6.48. Found: C, 65.11; H, 6.38.

Workup

  1. additionis added dropwise over 20 min
  2. additionAfter the addition
  3. additionAfter an additional 2 h at -40° C. the brown reaction mixture is carefully poured
  4. customonto crushed ice
  5. extractionextracted with CH2 Cl2 (2×500 mL)
  6. dry with materialthe combined extracts dried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c8791f40e0a0496e8713f52e8223e0fa
Source dataset
uspto-grants-1998_01
Patent number
US05708001

Reaction notes

Loading…