Bromine → HCID 58028434, compound

HRID 1943523Notes

Reaction equation

HRID 1943523 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% solution 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 solution, sat. sodium hydrogencarbonate solution and sat. sodium chloride solution. The solution is dried using sodium sulfate and evaporated to dryness. 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 solution, sat. sodium hydrogencarbonate solution and sat. sodium chloride solution
  3. customThe solution is dried
  4. customevaporated to dryness
  5. customThe crude product is purified by column chromatography (SiO2, n-heptane)

Sources & evidence

ORD record
ord-5e316dcf72ef436ca806c69517fbd775
Source dataset
uspto-grants-2013_03
Patent number
US08394293B2

Reaction notes

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