Trifluoroacetic acid → HCID 68502963, compound

HRID 2354115Notes

Reaction equation

HRID 2354115 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1[O:17]C(=O)C.F[C:22](F)(F)[C:23](O)=O.CO[CH2:30][N:31]([Si](C)(C)C)C>C1(C)C=CC=CC=1>[CH3:30][N:31]1[CH2:23][CH2:22][C@@H:9]([C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[OH:17])[C@@H:8]1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 44139027Phenol, 2-[(1E)-2-(2-bromophenyl)ethenyl]-4-chloro-, 1-acetateHCID 86617526HCID 86617526, compound

Product 1

HCID 68502963HCID 68502963, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

trans-2-Bromo-2′-acetoxy-5′-chlorostilbene (26 g, 73 mmol) was slurried in toluene (91 ml) at 33° C. Trifluoroacetic acid (200 microliters) was added. The N-methoxymethyl-N-trimethylsilyl-N-methylamine (14.5 g; 89.7 mmol) was added to the reaction mixture over 90 minutes. After addition, the reaction was washed with water (25 ml). The toluene was removed by vacuum distillation. Ethanol (30 ml) was added and removed under reduced pressure. The oil was dissolved in methanol (90 ml). Potassium hydroxide (5 grams in 25 ml water)) was added. The product began to precipitate immediately. After 30 minutes, the pH was adjusted to 8-9 with 3N HCl (8 ml). Added water (10 ml) and cooled to less than 10° C. Filtered and washed with 1:1 methanol: water. Dried in vacuum to 26.0 grams (96% yield). Purity according to HPLC is 98% a/a.

Workup

  1. additionAfter addition
  2. washthe reaction was washed with water (25 ml)
  3. customThe toluene was removed by vacuum distillation
  4. additionEthanol (30 ml) was added
  5. customremoved under reduced pressure
  6. dissolutionThe oil was dissolved in methanol (90 ml)
  7. additionPotassium hydroxide (5 grams in 25 ml water)) was added
  8. customto precipitate immediately
  9. temperatureAdded water (10 ml) and cooled to less than 10° C
  10. filtrationFiltered
  11. washwashed with 1:1 methanol
  12. customDried in vacuum to 26.0 grams (96% yield)

Sources & evidence

ORD record
ord-2b01e92ede874a0d857169e93da74062
Source dataset
uspto-grants-2010_07
Patent number
US07750167B2

Reaction notes

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