Bromine → HCID 58028434, compound

HRID 449737Notes

Reaction equation

HRID 449737 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[Li]CCCC.[Br:23]Br>C1COCC1.CC(OC)(C)C>[Br:23][C:15]1[S:14][C:13]([C:4]2[CH:5]=[CH:6][C:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[C:2]([F:1])[CH:3]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 24408BromineHCID 58028440HCID 58028440, compoundHCID 178418339Butyllithium

Product 1

HCID 58028434HCID 58028434, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
-70 °C

Procedure

20.0 g (80.5 mmol) of 2-(3-fluoro-4-pentylphenyl)thiophene are initially introduced in 200 ml of THF, and 50.0 ml of n-BuLi (79.6 mmol, 15% soln. in hexane) are added dropwise to the solution at a temperature in the range 0-5° C. After 1 h at 0° C., the batch is cooled to −70° C., and 4.1 ml (80.0 mmol) of bromine are metered in. When the addition is complete, the mixture is stirred at 0° C. for 1 h. The batch is diluted with MTBE and washed successively with 2 N HCl, 10% sodium hydrogensulfite soln., sat. sodium hydrogencarbonate soln. and sat. sodium chloride soln. The solution is dried using sodium sulfate and concentrated to completion. The crude product is purified by column chromatography (SiO2, n-heptane). 2-Bromo-5-(3-fluoro-4-pentylphenyl)thiophene is obtained as a yellowish liquid.

Workup

  1. additionWhen the addition
  2. washwashed successively with 2 N HCl, 10% sodium hydrogensulfite soln
  3. customThe solution is dried
  4. concentrationconcentrated to completion
  5. customThe crude product is purified by column chromatography (SiO2, n-heptane)

Sources & evidence

ORD record
ord-89426444671b448c86a2a7cf2542fc96
Source dataset
uspto-grants-2013_07
Patent number
US08486297B2

Reaction notes

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