Phosgene → HCID 11037855, compound

HRID 362588Notes

Reaction equation

HRID 362588 reaction equation
C[Si](C)(C)[O:3][CH2:4][CH:5]1[C:17]2[C:12](=[C:13]3[CH:25]=[CH:24][CH:23]=[CH:22][C:14]3=[C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]3=2)[C:11]2[C:6]1=[C:7]1[CH:33]=[CH:32][CH:31]=[CH:30][C:8]1=[C:9]1[CH:29]=[CH:28][CH:27]=[CH:26][C:10]1=2.[C:36](Cl)([Cl:38])=[O:37]>ClCCl>[Cl:38][C:36]([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[C:13]3[CH:25]=[CH:24][CH:23]=[CH:22][C:14]3=[C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]3=2)[C:11]2[C:6]1=[C:7]1[CH:33]=[CH:32][CH:31]=[CH:30][C:8]1=[C:9]1[CH:29]=[CH:28][CH:27]=[CH:26][C:10]1=2)=[O:37]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 15020964HCID 15020964, compound

Product 1

HCID 11037855HCID 11037855, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 17-(trimethylsilyl)oxymethyl-tetrabenzo(a,c,g,i)fluorene (0.177 g, 0.38 mmol) in dichloromethane (5 ml) was added phosgene (1.5 ml, 2.9 mmol; 7.5 equiv; 1.93M in toluene). The reaction mixture was heated under reflux for 2 h and then stirred at room temperature for 48 h, under nitrogen. The solvent was removed in vacuo to give compound (37) as a yellow solid which was recrystallized from dichloromethane/n-hexane (36.9 mg, 21%); m.p. 188°-189° C.; (Found: C, 80.9; H, 4.29; N, 0.45 C31H19O2Cl requires: C, 81.1; H, 4.14%); νmax (CH2Cl2) 3060 (CH stretching, aromatic), 1775 (CO, chloroformate), 1610, 1500 (aromatic rings), 1160, 1140 (CO stretching) cm-1 ; δH (CDCl3, 200 MHz) 8.79-8.60 (6H, m, aromatic), 8.20-8.15 (2H, m, aromatic), 7.76-7.57 (8H, m, aromatic), 5.17 (1H, t, 3J=5.7 Hz, CH), 4.77 (2H, d, 3J=5.7 Hz, CH2); δc (CDCl3, 50 MHz) 150.5 (CO, chloroformate), 140.3, 137.2, 131.6, 130.5, 128.2, 127.7 (quaternary aromatic C's), 127.5, 127.0, 126.3, 126.2, 125.1, 124.5, 123.5, 123.4 (aromatic CH's), 74.6(CH2), 46.5(CH).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 h
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ced6c059b2f54c5f92754c09cd4ef5df
Source dataset
uspto-grants-1999_02
Patent number
US05869605

Reaction notes

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