N-bromobutanimide → 3-Bromo-2-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene

HRID 2272245Notes

Reaction equation

HRID 2272245 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[S:14][C:13]2[CH2:15][CH2:16][CH2:17][CH2:18][C:12]=2[CH:11]=1>C(#N)C.C(=O)(O)[O-].[Na+]>[Br:1][C:11]1[C:12]2[CH2:18][CH2:17][CH2:16][CH2:15][C:13]=2[S:14][C:10]=1[CH3:9]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 122042872-Methyl-4,5,6,7-tetrahydrobenzo[b]thiophene

Product 1

HCID 584872903-Bromo-2-methyl-4,5,6,7-tetrahydrobenzo[b]thiopheneYield 67,776.297%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 516892Sodium BicarbonateSolvent

Procedure

N-bromosuccinimide (52 mg, 0.3 mmol) was added to a solution of 238 (42 mg, 0.3 mmol) in acetonitrile (1.4 mL). The resulting mixture was stirred at room temperature for 2 days. The mixture was diluted with saturated sodium bicarbonate solution (10 mL) and extracted with dichloromethane (3×5 mL). The combined organic extracts were dried with sodium sulfate and concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-5% ethyl acetate in hexane) provided 239 (47 g, 73%) as a liquid.

Workup

  1. extractionextracted with dichloromethane (3×5 mL)
  2. dry with materialThe combined organic extracts were dried with sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a1072da345e3477b8b5ec2355851b66b
Source dataset
uspto-grants-2015_09
Patent number
US09120751B2

Reaction notes

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