Toluene → HCID 12134724, compound

HRID 1068208Notes

Reaction equation

HRID 1068208 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN([CH:14]([CH3:16])[CH3:15])C(C)C.[S:17]([O:24]S(C(F)(F)F)(=O)=O)([C:20]([F:23])([F:22])[F:21])(=[O:19])=[O:18].CCO[CH2:35][CH3:36].[CH2:37](Cl)Cl>>[F:21][C:20]([F:23])([F:22])[S:17]([O:24][C:3]1[CH:4]=[CH:5][CH:6]=[C:1]([CH2:7][C:15]2[CH:14]=[CH:16][CH:36]=[CH:35][CH:37]=2)[CH:2]=1)(=[O:19])=[O:18]

Participants

6

Reactant 5

HCID 1140TolueneHCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 67749Trifluoromethanesulfonic anhydrideHCID 81531Diisopropylethylamine

Product 1

HCID 12134724HCID 12134724, compoundYield 83%

Conditions

Temperature
0 °C

Procedure

To a solution of 545 mg (2.9 mmol) of (3-hydroxyphenyl), phenylmethane (from Step A) and 0.62 mL (3.5 mmol) of DIEA in 6 mL of CH2Cl2 at −78° C. was added 0.5 mL (2.9 mmol) of triflic anhydride. After warming to 0° C. and stirring for 10 minutes, the reaction was poured into 100 mL of Et2O and washed with 100 mL of brine and 100 mL of NaHCO3. After separating phases, the organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by flash chromatography eluting with 19:1 v/v hexane/Et2O to yield 779 mg (83%) of the title compound: Rf: 0.62 (9:1 v/v hexanes/Et2O); 1H NMR (300 MHz, CDCl3) δ4.01 (s, 2H), 7.08-7.37 (m, 9H).

Workup

  1. washwashed with 100 mL of brine and 100 mL of NaHCO3
  2. customAfter separating phases
  3. dry with materialthe organic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography
  6. washeluting with 19:1 v/v hexane/Et2O

Sources & evidence

ORD record
ord-b1a9e25bbcea49dfa9e030b168b08017
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

Loading…