Water → HCID 59475971, compound

HRID 1470057Notes

Reaction equation

HRID 1470057 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:21])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]3[CH2:18][C:17]3([Br:20])[Br:19])=[CH:12][CH:11]=2)=O)[CH:7]=1.C([SiH](CC)CC)C.O>FC(F)(F)C(O)=O.FC(F)(F)S(O)(=O)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:21])=[C:6]([CH2:8][C:10]2[CH:15]=[CH:14][C:13]([CH:16]3[CH2:18][C:17]3([Br:20])[Br:19])=[CH:12][CH:11]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 12052TriethylsilaneHCID 59475970HCID 59475970, compound

Product 1

HCID 59475971HCID 59475971, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 62406Trifluoromethanesulfonic acidCatalystHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
30 °C

Procedure

Trifluoromethanesulfonic acid (0.5 g, 0.0033 mol) was added slowly to a stirred solution of Example 4B (104 g, 0.211 mol) and triethylsilane (66.8 g, 0.574 mol) in trifluoroacetic acid (300 mL) cooled to 30° C. in a water-bath. The reaction became refluxed. After 0.5 h, the water bath was replaced by an oil bath. The reaction mixture was heated to reflux for 3 h. After cooling to room temperature, the reaction mixture was allowed to stir for another 1 h. The solid was filtered, washed with hexane (100 mL) and dried under vacuum at 30° C. to get the desired product as a pale gray solid (86.4 g, yield 85%) 1H NMR (CDCl3, 400 MHz): δ 7.28˜7.34 (m, 3H), 7.18˜7.25 (m, 4H), 4.08 (s, 1H), 2.93˜2.98 (m, 1H), 2.13˜2.17 (m, 1H), 2.00˜2.03 (m, 1H).

Workup

  1. temperatureThe reaction became refluxed
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 3 h
  4. temperatureAfter cooling to room temperature
  5. filtrationThe solid was filtered
  6. washwashed with hexane (100 mL)
  7. customdried under vacuum at 30° C.

Sources & evidence

ORD record
ord-dafded45de724d08a62a8ae195d60f97
Source dataset
uspto-grants-2015_04
Patent number
US09006403B2

Reaction notes

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