Diethyl Ether → HCID 86714198, compound

HRID 628209Notes

Reaction equation

HRID 628209 reaction equation
[S:1]1[C:5]([CH2:6]O)=[CH:4][C:3]2[CH:8]=[C:9]3[C:14](=[CH:15][C:2]1=2)[CH:13]=[CH:12][CH:11]=[CH:10]3.C(OCC)C.P(Br)(Br)[Br:22]>CO>[Br:22][CH2:6][C:5]1[S:1][C:2]2[CH:15]=[C:14]3[C:9](=[CH:8][C:3]=2[CH:4]=1)[CH:10]=[CH:11][CH:12]=[CH:13]3

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24614Phosphorus tribromideHCID 86714197HCID 86714197, compound

Product 1

HCID 86714198HCID 86714198, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Naptho[2,3-b]thiophene-2-methanol (12, 2.71 g, 12.6 mmol., 1.00 equiv.) and diethyl ether (76 mL) were added to a 280 mL Schlenk flask and the mixture was cooled to 0° C. Phosphorus tribromide was added (0.89 mL, 9.5 mmol., 0.75 equiv.) and the mixture was left to warm slowly to room temperature while stirring for 16 hours. The mixture was diluted with methanol (300 mL) and the solids were collected by filtration and washed with methanol (50 mL), giving a beige solid (2.98 g, 85% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.27 (s, 1H), 8.23 (s, 1H), 7.97-7.86 (m, 2H), 7.52-7.43 (m, 2H), 7.41 (s, 1H), 4.81 (s, 2H).

Workup

  1. waitthe mixture was left
  2. temperatureto warm slowly to room temperature
  3. filtrationthe solids were collected by filtration
  4. washwashed with methanol (50 mL)

Sources & evidence

ORD record
ord-69d01706244443738a30abd40a7765ad
Source dataset
uspto-grants-2016_04
Patent number
US09312501B2

Reaction notes

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