Water → HCID 18687827, compound

HRID 1873196Notes

Reaction equation

HRID 1873196 reaction equation
Br[CH2:2][C:3]#[N:4].[Br:5][C:6]1[CH:11]=[C:10]([C:12]2[C:21]3[C:22]4[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=4[S:24][C:20]=3[C:19]([Br:29])=[C:18]3[C:13]=2[CH:14]=[CH:15][CH:16]=[CH:17]3)[CH:9]=[C:8]([Br:30])[C:7]=1[OH:31].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Br:5][C:6]1[CH:11]=[C:10]([C:12]2[C:21]3[C:22]4[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=4[S:24][C:20]=3[C:19]([Br:29])=[C:18]3[C:13]=2[CH:14]=[CH:15][CH:16]=[CH:17]3)[CH:9]=[C:8]([Br:30])[C:7]=1[O:31][CH2:2][C:3]#[N:4]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 108406542,6-Dibromo-4-(6-bromo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenol

Product 1

HCID 18687827HCID 18687827, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Bromoacetonitrile (0.25 mL, 3.56 mmol) was added to a room temperature, stirred suspension of 2,6-dibromo-4-(6-bromo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenol (1.0 g, 1.78 mmol) and potassium carbonate (0.615 g, 4.45 mmol) in DMF (5 mL). After 2.5 h, the reaction mixture was added to water, filtered, washed with water and triturated with petroleum ether. The solid was dried in vacuo at 80° C. to provide the title compound as a white solid (1.03 g, 96%): NMR (DMSO-d6); δ8.29 (d, J=8 Hz, 1 H), 8.08 (d, J=8 Hz, 1 H), 7.92 (s, 2 H), 7.80 (ddd, J=8, 7, 1 Hz, 1 H), 7.65-7.51 (m, 3 H), 7.27 (ddd, J=8, 7, 1 Hz, 1 H), 6.68 (d, J=8 Hz, 1 H), 5.36 (s, 2 H); MS (+FAB): [M+], 3 bromine isotope pattern, 599, 601, 603, 605; Anal. Calc. for C24H12Br3NOS: C, 47.87, H, 2.01, N, 2.33. Found: C, 47.83, H, 1.92, N, 2.32.

Workup

  1. filtrationfiltered
  2. washwashed with water
  3. customtriturated with petroleum ether
  4. customThe solid was dried in vacuo at 80° C.

Sources & evidence

ORD record
ord-58db999f0f12446e9be26ca0f93e57e1
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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