Tetrahydrofuran → HCID 22237523, compound

HRID 1281407Notes

Reaction equation

HRID 1281407 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1COCC1.C(Br)(Br)(Br)[Br:26].[CH2:30]([NH:42][C:43](=[O:63])[C:44]1[CH:49]=[C:48]([C:50]2[CH:55]=[CH:54][CH:53]=[C:52]([O:56][CH3:57])[CH:51]=2)[C:47]([O:58][CH2:59][CH2:60]O)=[C:46]([Br:62])[CH:45]=1)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>CCOC(C)=O>[CH2:30]([NH:42][C:43](=[O:63])[C:44]1[CH:49]=[C:48]([C:50]2[CH:55]=[CH:54][CH:53]=[C:52]([O:56][CH3:57])[CH:51]=2)[C:47]([O:58][CH2:59][CH2:60][Br:26])=[C:46]([Br:62])[CH:45]=1)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11205Carbon tetrabromide2×HCID 11776Triphenylphosphine3×HCID 22237429HCID 22237429, compound

Product 1

HCID 22237523HCID 22237523, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a flamed dried flask was added triphenylphosphine (98 mg, 0.373 mmol) and 1.5 mL anhydrous THF. This was stirred until all the triphenylphosphine had dissolved. Then CBr4 (123 mg, 0.373 mmol) was added. The reaction mixture was stirred for one-half hour at room temperature then it was cooled to ° C. before N-dodecyl-3-bromo-4-(2-hydroxyethoxy)-5-(3-methoxyphenyl)benzamide (200 mg, 0.373 mmol) was added. The cooling bath was removed after the addition was complete. After the reaction mixture had warmed up to room temperature, 0.2 eq each of triphenylphosphine (19.6 mg, 0.075 mmol) and CBr4 (24.8 mg, 0.075 mmol) were added. The reaction was stirred for one-half hour then the solvent was removed under vacuum to give a yellow semisolid. This material was subjected to flash chromatography (25% EtOAc:75% Hexanes) to yield 150 mg, 67% of a yellow oil. 1H NMR (CDCl3) δ 1.25 (t, J=8.13 Hz, 3H); 1.22-1.40 (m, 18H); 1.52-1.63 (m, 2H); 3.35 (t, J=8.18 Hz, 2H); 3.40 (q, J=6.54 Hz, 2H); 3.84-3.90 (m, 5H); 6.00 (m, 1H); 6.93 (dd, J=8.18 Hz, 2.45 Hz, 1H); 7.07-7.11 (m, 2H); 7.35 (t, J=8.18 Hz, 1H); 7.65 (d, J=2.45 Hz, 1H); 7.39 (d, J=2.45 Hz, 1H).

Workup

  1. customTo a flamed dried flask
  2. dissolutionhad dissolved
  3. temperatureit was cooled
  4. customThe cooling bath was removed
  5. additionafter the addition
  6. temperatureAfter the reaction mixture had warmed up to room temperature
  7. stirringThe reaction was stirred for one-half hour
  8. customthe solvent was removed under vacuum
  9. customto give a yellow semisolid

Sources & evidence

ORD record
ord-22453001d7f94cd6a22b45ac89eea0e1
Source dataset
uspto-grants-2002_09
Patent number
US06451827B2

Reaction notes

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