Benzyl Alcohol → HCID 18188911, compound

HRID 2269794Notes

Reaction equation

HRID 2269794 reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6]3[C:14]([O:15][CH:16]([F:18])[F:17])=[CH:13][CH:12]=[CH:11][C:7]=3[O:8][C:9](=[O:10])[C:4]=2[C:3]=1[Br:21].Cl[C:23](Cl)([O:25][C:26](=[O:32])OC(Cl)(Cl)Cl)Cl.C(O)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C1COCC1>[CH2:23]([O:25][C:26]([NH:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6]3[C:14]([O:15][CH:16]([F:18])[F:17])=[CH:13][CH:12]=[CH:11][C:7]=3[O:8][C:9](=[O:10])[C:4]=2[C:3]=1[Br:21])=[O:32])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 94429TriphosgeneHCID 12085086HCID 12085086, compound

Product 1

HCID 18188911HCID 18188911, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 27C (1.13 g, 3.19 mmol) in THF (100 mL) was treated with triphosgene (0.95 g, 3.19 mmol), heated at reflux for 4 hours, treated with benzyl alcohol, (3.44 g, 31.9 mmol), heated at reflux for 16 hours, cooled to room temperature, and concentrated to a fraction of its original volume. The solution was cooled to 0° C. and filtered to provide the desired product. MS (ESI(−)Q1MS) m/z 488 (M−H)−.

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 hours
  3. temperatureheated
  4. temperatureat reflux for 16 hours
  5. concentrationconcentrated to a fraction of its original volume
  6. temperatureThe solution was cooled to 0° C.
  7. filtrationfiltered

Sources & evidence

ORD record
ord-7c99054058d54597ba211e16ccca7bb9
Source dataset
uspto-grants-2001_12
Patent number
US06329534B1

Reaction notes

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