2-Bromophenol → HCID 17952544, compound

HRID 456454Notes

Reaction equation

HRID 456454 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[CH:9](C1CCN1O)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:27]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:32]=CC=C[CH:28]=1.[N:46](C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1.C(OCC)C>[CH:9]([N:46]1[CH2:32][CH:27]([O:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Br:1])[CH2:28]1)([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 72442-BromophenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 17952563HCID 17952563, compound

Product 1

HCID 17952544HCID 17952544, compoundYield 61.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Bromophenol (3.8 mL, 32.6 mmol), benzhydrylazetidinol (7.8 g, 32.6 mmol) and triphenylphosphine (12.8 g, 28.9 mmol) were dissolved in THF (200 mL) under nitrogen and cooled to 0° C. Diisopropyl azodicarboxylate (9.7 mL, 48.9 mmol) was added dropwise over 30 minutes, and the mixture was stirred for about 96 hours at r.t. Diethyl ether (400 mL) was added, and the solution was washed with 5 N NaOH (2×50 mL) and brine (50 mL), and then dried over magnesium sulfate and concentrated to a colorless oil. Purification by silica gel chromatography (4:1 hexanes/ethyl acetate) gave the title compound as a colorless oil (7.0 g, 55%).

Workup

  1. washthe solution was washed with 5 N NaOH (2×50 mL) and brine (50 mL)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated to a colorless oil
  4. customPurification by silica gel chromatography (4:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-e362bb39d9984bc08b02928ec6afed2f
Source dataset
uspto-grants-2007_03
Patent number
US07186715B2

Reaction notes

Loading…