Sodium borohydride → 5-Bromo-2-chloro-1-(5-(2-pyridyl)-2-thienylmethyl)benzene

HRID 1514529Notes

Reaction equation

HRID 1514529 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:21])=[C:6]([CH:8]([C:10]2[S:11][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[CH:13][CH:14]=2)O)[CH:7]=1.[BH4-].[Na+]>FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:21])=[C:6]([CH2:8][C:10]2[S:11][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[CH:13][CH:14]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 666073255-Bromo-2-chlorophenyl-5-(2-pyridyl)-2-thienylmethanol

Product 1

HCID 666072295-Bromo-2-chloro-1-(5-(2-pyridyl)-2-thienylmethyl)benzeneYield 71.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent2×

Procedure

2-(2-Pyridyl)thiophene and 5-bromo-2-chlorobenzaldehyde obtained in Reference Example 16-(1) were treated in a manner similar to Reference Example 7-(1) to give 5-bromo-2-chlorophenyl-5-(2-pyridyl)-2-thienylmethanol as colorless powder. APCI-Mass m/Z 380/382 (M+H). (2) A solution of the above 5-bromo-2-chlorophenyl-5-(2-pyridyl)-2-thienylmethanol (3.52 g) in trifluoroacetic acid (45 ml) was added to a solution of sodium borohydride (1.75 g) in trifluoroacetic acid (45 ml), and the mixture was stirred at room temperature for 4 hours. Trifluoroacetic acid was evaporated under reduced pressure. The residue was basified with an aqueous potassium hydroxide solution, and extracted with diethyl ether. The extract was dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1-4:1) to give 5-bromo-2-chloro-1-(5-(2-pyridyl)-2-thienylmethyl)benzene (2.42 g) as a colorless solid. APCI-Mass m/Z 364/366 (M+H).

Workup

  1. customTrifluoroacetic acid was evaporated under reduced pressure
  2. extractionextracted with diethyl ether
  3. dry with materialThe extract was dried over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1-4:1)

Sources & evidence

ORD record
ord-e75ee286160f47e5bc2393ddf0d73550
Source dataset
uspto-grants-2012_07
Patent number
US08222219B2

Reaction notes

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