1-(3-Bromo-4-fluorophenylthio)propan-2-one → 6-Bromo-5-fluoro-3-methylbenzo[b]thiophene

HRID 523576Notes

Reaction equation

HRID 523576 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:9][CH2:10][C:11](=O)[CH3:12])[CH:5]=[CH:6][C:7]=1[F:8]>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]2[C:11]([CH3:12])=[CH:10][S:9][C:4]=2[CH:3]=1

Participants

3

Reactant 1

HCID 667645651-(3-Bromo-4-fluorophenylthio)propan-2-one

Product 1

HCID 709819996-Bromo-5-fluoro-3-methylbenzo[b]thiopheneYield 72%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Using analogous reagents and reaction conditions as described in Example 24 for the preparation of I-24b above, 1-(3-bromo-4-fluoro-phenylsulfanyl)-propan-2-one (I-29a: 2.1 g, 8.015 mmol) in toluene (10 mL) was cyclized with polyphosphoric acid (8 g) to yield crude product which was purified by column chromatography on silica gel (100% hexane) to afford 1.4 g of product (72% yield).

Workup

  1. customreagents and reaction conditions
  2. customto yield crude product which
  3. customwas purified by column chromatography on silica gel (100% hexane)

Sources & evidence

ORD record
ord-c8b515f4d1a04a249ebfc7d37530b64d
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

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