4-Fluorophenol → HCID 23512174, compound

HRID 354522Notes

Reaction equation

HRID 354522 reaction equation
[CH2:1]([N:8]([CH2:16][CH2:17][OH:18])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23](O)=[CH:22][CH:21]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH2:1]([N:8]([CH2:16][CH2:17][O:18][C:23]1[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=1)[C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 97324-FluorophenolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 10753247Tert-butyl N-benzyl-N-(2-hydroxyethyl)carbamate

Product 1

HCID 23512174HCID 23512174, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(N-benzyl-N-tert-butoxycarbonylamino)ethanol (6.85 g, 27.3 mmol), 4-fluorophenol (3.07 g, 27.3 mmol) and PPh3 (7.83 g, 30.0 mmol) in THF (100 mL) was added DIAD (6.00 mL, 30.0 mmol) at room temperature. After being stirred for 3 hr, the reaction mixture was concentrated. Chromatography of the residue with hexane-EtOAc (8:1, v/v) as eluent gave 1-[2-(N-benzyl-N-tert-butoxycarbonylamino)ethoxy]-4-fluorobenzene (8.19 g, 64%) as a yellow oil. 1H-NMR (CDCl3) δ1.42-1.50 (m, 9H), 3.41-3.67 (m, 2H), 3.92-4.11 (m, 2H), 4.51-4.63 (m, 2H), 6.73-6.85 (m, 2H), 6.89-6.98 (m, 2H), 7.24 (m 5); FAB-MS m/z 346 (M++1).

Workup

  1. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-c25170a64298459a9d21849cb9609cad
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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