Bromobenzene → 1-Phenylazetidin-3-ol

HRID 1176587Notes

Reaction equation

HRID 1176587 reaction equation
CC(C)([O-])C.[Na+].Cl.[OH:8][CH:9]1[CH2:12][NH:11][CH2:10]1.Br[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[C:14]1([N:11]2[CH2:12][CH:9]([OH:8])[CH2:10]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 7961BromobenzeneHCID 634876Binap, (A+-)-HCID 27592903-Hydroxyazetidine hydrochlorideHCID 23676156Sodium t-butoxide

Product 1

HCID 224365261-Phenylazetidin-3-ol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

The mixture of 1.053 g of sodium tert-butoxide, 0.500 g of 3-hydroxyazetidine hydrochloride, 0.864 g of bromobenzene and 9 ml of toluene is initially charged under argon with stirring in a Schlenk apparatus. The mixture is admixed with a solution of 0.234 g of (+,−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl and dipalladiumtris(dibenzylidenacetone)-chloroform complex in 2 ml of toluene (prepared in a Schlenk apparatus under argon) and the reaction mixture is stirred at 70° C. for 5 hours. The reaction mixture is cooled, poured onto ice-water (50 ml) and extracted with tert-butyl methyl ether (2×100 ml). The organic phases are washed with brine (50 ml), dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a reddish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.25 (1:1 EtOAc-heptane). Rt=2.01.

Workup

  1. additionis initially charged under argon
  2. stirringthe reaction mixture is stirred at 70° C. for 5 hours
  3. temperatureThe reaction mixture is cooled
  4. additionpoured onto ice-water (50 ml)
  5. extractionextracted with tert-butyl methyl ether (2×100 ml)
  6. washThe organic phases are washed with brine (50 ml)
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-f33dc976dfcf4776a91b7804c3a44379
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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