Hydrochloric Acid → HCID 70197424, compound

HRID 1873202Notes

Reaction equation

HRID 1873202 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[C:7]([C:9]2[C:18]3[C:19]4[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=4[S:21][C:17]=3[C:16]([Br:26])=[C:15]3[C:10]=2[CH:11]=[CH:12][CH:13]=[CH:14]3)[CH:6]=[C:5]([Br:27])[C:4]=1[O:28][P:29](=[O:40])([O:35]C(C)(C)C)[O:30]C(C)(C)C>O1CCOCC1>[Br:2][C:3]1[CH:8]=[C:7]([C:9]2[C:18]3[C:19]4[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=4[S:21][C:17]=3[C:16]([Br:26])=[C:15]3[C:10]=2[CH:11]=[CH:12][CH:13]=[CH:14]3)[CH:6]=[C:5]([Br:27])[C:4]=1[O:28][P:29](=[O:30])([OH:35])[OH:40]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 70204886HCID 70204886, compound

Product 1

HCID 70197424HCID 70197424, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

HCl (4 N in dioxane, 1.5 mL, 6 mmol) was added to a room temp[erature, stirred solution of phosphoric acid di-tert-butyl ester 2,6-dibromo-4-(6-bromo-benzo [b]naphtho[2,3-d]thiophen-11-yl)-phenyl ester (0.290 g, 0.384 mmol) in dioxane (6 mL). After 4.5 h, the solvent was removed and the solid was triturated with ether, petroleum ether and dried in vacuo to provide the title compound as a white solid (0.220, 86%): NMR (DMSO-d6); δ8.29 (d, J=8 Hz, 1 H), 8.08 (d, J=8 Hz, 1 H), 7.83 (s, 2 H), 7.80 (ddd, J=8, 7, 1 Hz, 1 H), 7.64 (ddd, J=8, 7, 1 Hz, 1 H), 7.56-7.51 (m, 2 H), 7.26 (ddd, J=8, 7, 1 Hz, 1 H), 6.71 (d, J=8 Hz, 1 H); MS (+FAB): [M+], 3 bromine isotope pattern, 640, 642, 644, 646; Anal. Calc. for C22H12Br3O4PS: C, 41.09, H, 1.88, N, 0.00. Found: C, 41.71, H, 2.22, N, 0.07.

Workup

  1. customthe solvent was removed
  2. customthe solid was triturated with ether, petroleum ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-2c171d899dde47909e550d1a19a1edc5
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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