1,8-Diazabicyclo(5.4.0)undec-7-ene → 6-Bromo-4-fluoro-1-benzothiophene

HRID 572406Notes

Reaction equation

HRID 572406 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:14])[C:5]2[CH:9]=[C:8](C(O)=O)[S:7][C:6]=2[CH:13]=1.C1CCN2C(=NCCC2)CC1>CC(N(C)C)=O>[Br:1][C:2]1[CH:3]=[C:4]([F:14])[C:5]2[CH:9]=[CH:8][S:7][C:6]=2[CH:13]=1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 709828206-Bromo-4-fluoro-1-benzothiophene-2-carboxylic acid

Product 1

HCID 709821066-Bromo-4-fluoro-1-benzothiopheneYield 97%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Using analogous reaction condition and reagents as described in Example 25 for the preparation of I-25c above, 6-bromo-4-fluoro-benzo[b]thiophene-2-carboxylic acid (I-26c: 1.8 g, 6.47 mmol) in DMA (4 mL) and DBU (4.0 g, 26.54 mmol) were heated in microwave to afford the crude product. Purification by column chromatography on silica gel (100% hexane) afforded 1.45 g of the product (97% yield).

Workup

  1. temperaturewere heated in microwave
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (100% hexane)

Sources & evidence

ORD record
ord-9cbb22901b2f4732bb9e45a1a5b58a4d
Source dataset
uspto-grants-2015_05
Patent number
US09029399B2

Reaction notes

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