(Diethylamino)sulfur trifluoride → HCID 86730298, compound

HRID 1053958Notes

Reaction equation

HRID 1053958 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.C(N(S(F)(F)[F:19])CC)C>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. Diethylaminosulfur trifluoride (0.433 mL, 3.27 mmol) was then slowly added To a solution and the resultant mixture was stirred at ambient temperature overnight. At which time, an additional 0.5 eq of DAST was added and stirred for an additional 4 hours. The reaction mixture was purified directly by MPLC on silica gel (eluting with 5% ethyl acetate in hexanes) to afford the title compound. 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. customThe reaction mixture was purified directly by MPLC on silica gel (eluting with 5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-3517dd3485444622ad08c21989155193
Source dataset
uspto-grants-2016_07
Patent number
US09394282B2

Reaction notes

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