4-Chlorophenol → 4-(4-Chlorophenoxymethyl)-benzylazide
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OC(C)C)=O)=O)(C)C.[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=1.[N:42]([CH2:45][C:46]1[CH:51]=[CH:50][C:49]([CH2:52]O)=[CH:48][CH:47]=1)=[N+:43]=[N-:44]>C1COCC1>[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH2:52][C:49]2[CH:48]=[CH:47][C:46]([CH2:45][N:42]=[N+:43]=[N-:44])=[CH:51][CH:50]=2)=[CH:37][CH:36]=1Participants
Conditions
- Temperature
- -40 °C
Procedure
Triphenylphosphine (4.33 g, 16.5 mmol) was dissolved in dry THF (20 mL) under an atmosphere of argon. After cooling to −40° C., diisopropyl-azodicarboxylate (DIAD, 3.2 mL, 16.5 mmol) was added and the mixture was stirred at −40° C. for 10 min. A solution of 4-chlorophenol (2.12 g, 16.5 mmol) and (4-azidomethyl-phenyl)-methanol (2.45 g, 15 mmol) in dry THF (10 mL) was added dropwise. After addition, the cooling bath was removed and stirring was continued for 1 h. The solution was diluted with Et2O (150 mL) and washed with pH-7-phosphate buffer solution (1×50 mL). The organic layer was dried over Na2SO4, filtered and evaporated under reduced pressure. The resulting residue was purified by flash chromatography (2-3% EtOAc in hexane) to give the title compound.
Workup
- additionAfter addition
- customthe cooling bath was removed
- stirringstirring
- waitwas continued for 1 h
- additionThe solution was diluted with Et2O (150 mL)
- washwashed with pH-7-phosphate buffer solution (1×50 mL)
- dry with materialThe organic layer was dried over Na2SO4
- filtrationfiltered
- customevaporated under reduced pressure
- customThe resulting residue was purified by flash chromatography (2-3% EtOAc in hexane)
Sources & evidence
- ORD record
- ord-e972db52186e44649e96bc77cbd1a831
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08450348B2
Reaction notes
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