Chlorosuccinimide → (2-Bromo-5-chlorothiophen-3-yl)methanol

HRID 870029Notes

Reaction equation

HRID 870029 reaction equation
[Br:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH2:7][OH:8].[Cl:9]N1C(=O)CCC1=O>C1COCC1.O>[Br:1][C:2]1[S:3][C:4]([Cl:9])=[CH:5][C:6]=1[CH2:7][OH:8]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 12479010(2-Bromothiophen-3-yl)methanol

Product 1

HCID 57900970(2-Bromo-5-chlorothiophen-3-yl)methanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromo-3-hydroxymethylthiophene from Example 1, Step 1 (13.0 g, 67.3 mmol) in THF (100 mL) and water (10 mL) was added N-chlorosuccinimide (9.88 g, 74.0 mmol) and the mixture was stirred at r.t. for 5 h and concentrated in vacuo. The residue was worked up as above to afford the desired product. The crude product was used directly.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-127fbcdd4fee4fa897c12acf1cd519ff
Source dataset
uspto-grants-2015_03
Patent number
US08969394B2

Reaction notes

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