Phosgene → 9(+)-Fluorenylethyl chloroformate

HRID 440340Notes

Reaction equation

HRID 440340 reaction equation
[C:1](Cl)([Cl:3])=[O:2].[CH:5]1[C:17]2[CH:16]([CH2:18][CH2:19][OH:20])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[CH:8]=[CH:7][CH:6]=1>C1(C)C=CC=CC=1>[Cl:3][C:1]([O:20][CH2:19][CH2:18][CH:16]1[C:17]2[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=2[C:10]2[C:15]1=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:2]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 10921761Fluorene-9-ethanol

Product 1

HCID 149683719(+)-Fluorenylethyl chloroformate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A phosgene solution (12.4 ml of a 1.93M solution in toluene) was added dropwise with stirring to a solution of 2-(9-fluorenyl)ethanol (1.26 g, 6 mmol). After 0.5 hours the solution was put under vacuum to remove the phosgene, and concentrated to give 2-(9-fluorenyl)ethyl chloroformate (1.64 g, 6 mmol). This was dissolved in 10 ml dioxane, and to it added dropwise a solution of anthranilic acid (0.85 g, 6.2 mmol) and potassium carbonate (0.86 g, 6.2 mmol) in 15 ml water. After 3 hours, the dioxane was evaporated, and the solution diluted with an equal amount of water. Acidification with 10% HCl yielded a white precipitate which was washed with water and dried. (1.98 g, 88%), mp 177° C. IR(KBr) 3175, 1709, 1684, 1594, 1537, 1450, 1380, 1301, 1259, 1205, 1146, 1049, 753, 740 cm-1. 1H NMR (300 MHz, CDCl3) δ 2.46 (q, 2H, J=6.8), 4.14 (t, 3H, J=6.8), 7.10 (t, 1H, J=6.5), 8.46 (m, 13H), 10.13 (s, 1H). Anal. calcd for C23H19NO4 : C, 73.98; H, 5.13; N, 3.75. Found: C, 73.87; H, 5.19; N, 3.73.

Workup

  1. customto remove the phosgene
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-30ecf54bee47473c91fac9c977fa122c
Source dataset
uspto-grants-1996_05
Patent number
US05519043

Reaction notes

Loading…