4-Chlorophenol → 2-[3-(4-Chloro-phenoxymethyl)-benzyl]-phthalimide

HRID 2097354Notes

Reaction equation

C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=1.O[CH2:43][C:44]1[CH:45]=[C:46]([CH:59]=[CH:60][CH:61]=1)[CH2:47][C:48]12[CH:58]=[CH:57][CH:56]=[CH:55][CH:49]1[C:50]([NH:52][C:53]2=[O:54])=[O:51]>C1COCC1>[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH2:43][C:44]2[CH:45]=[C:46]([CH:59]=[CH:60][CH:61]=2)[CH2:47][C:48]23[CH:58]=[CH:57][CH:56]=[CH:55][CH:49]2[C:50]([NH:52][C:53]3=[O:54])=[O:51])=[CH:37][CH:36]=1

Participants

Conditions

Temperature: -40 °C

Procedure

Triphenylphosphine (280 mg, 1.07 mmol) was dissolved in dry THF (2 mL) under an atmosphere of argon. After cooling to −40° C., DIAD (0.21 mL, 1.07 mmol) was added and the mixture was stirred at −40° C. for 10 min. A solution of 4-chlorophenol (138 mg g, 1.07 mmol) and 2-(3-hydroxymethylbenzyl)-phthalimide (261 mg, 0.98 mmol) in dry THF (3 mL) was added dropwise. After addition, the cooling bath was removed and stirring was continued for 2 h. The solution was diluted with Et2O (40 mL) and washed with pH-7-phosphate buffer solution (1×20 mL). The organic layer was dried over Na2SO4, filtered and evaporated under reduced pressure. The resulting residue was purified by flash chromatography (EtOAc/hexane 1:5) to give the title compound.

Workup

additionAfter addition
customthe cooling bath was removed
stirringstirring
waitwas continued for 2 h
additionThe solution was diluted with Et2O (40 mL)
washwashed with pH-7-phosphate buffer solution (1×20 mL)
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
customevaporated under reduced pressure
customThe resulting residue was purified by flash chromatography (EtOAc/hexane 1:5)

Sources & evidence

ORD record: ord-ff06b3927e4747d985c933d4d4f468cb
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450348B2

Reaction notes

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