(Diethylamino)sulfur trifluoride → HCID 86730298, compound

HRID 1852452Notes

Reaction equation

HRID 1852452 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:12])([CH3:11])[CH2:9]O)=[CH:4][CH:3]=1.CCN(S(F)(F)[F:19])CC>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:12])([CH3:11])[CH2:9][F:19])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluoride2×HCID 128051244-Bromo-beta,beta-dimethylbenzeneethanol

Product 1

HCID 86730298HCID 86730298, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-bromophenyl)-2-methylpropan-1-ol (500 mg, 2.182 mmol) was dissolved in Dichloromethane (7.2 mL) in a 20 mL vial. DAST (0.433 mL, 3.27 mmol) was then slowly added to the solution. Stirred at ambient temperature overnight. TLC showed presence of starting material. Another 0.5 eq. of DAST was added and stirred for 4 hours. TLC then showed consumption of starting material. The reaction was loaded directly on a silica column and the column was then dried out. Purified with a Teledyne Isco Combiflash Rf purification system using a gradient of 5% EtOAc/hexanes. Isolated 1-bromo-4-(1-fluoro-2-methylpropan-2-yl)benzene as a clear liquid. 1H NMR (500 MHz, CDCl3) δ 7.43-7.42 (d, 2H), 7.10-7.09 (d, 2H), 2.88 (s, 1H), 2.83 (s, 1H), 1.35 (s, 3H), 1.30 (s, 3H).

Workup

  1. stirringstirred for 4 hours
  2. customconsumption of starting material
  3. customthe column was then dried out
  4. customPurified with a Teledyne Isco Combiflash Rf purification system

Sources & evidence

ORD record
ord-2e3e9a8e3ce347b4a75ce18d8a90524b
Source dataset
uspto-grants-2015_02
Patent number
US08962608B2

Reaction notes

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