Dimethylformamide → 8-bromo-4H-thieno[3,2-c]chromene-2-carbonyl chloride

HRID 628098Notes

Reaction equation

HRID 628098 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[O:8][CH2:7][C:6]3[CH:12]=[C:13]([C:15]([OH:17])=O)[S:14][C:5]=3[C:4]=2[CH:3]=1.C(Cl)(=O)C([Cl:21])=O.CN(C)C=O>ClCCl>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[O:8][CH2:7][C:6]3[CH:12]=[C:13]([C:15]([Cl:21])=[O:17])[S:14][C:5]=3[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 57900438HCID 57900438, compound

Product 1

HCID 579004048-bromo-4H-thieno[3,2-c]chromene-2-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 8-bromo-4H-thieno[3,2-c]chromene-2-carboxylic acid 3bp (1.50 g, 4.82 mmol, 1 equiv) in dichloromethane (45 mL) at 24° C. was sequentially added oxalyl chloride (3.1 mL, 6.3 mmol, 1.3 equiv, 2.0 M in dichloromethane) and N,N-dimethylformamide (56 μL, 0.72 mmol, 0.15 equiv), as in General Procedure B. After 2 hr, the clear yellow solution was concentrated in vacuo (˜20 mm Hg) to afford crude 4bp.

Workup

  1. concentrationthe clear yellow solution was concentrated in vacuo (˜20 mm Hg)
  2. customto afford crude 4bp

Sources & evidence

ORD record
ord-8e028575bba544f79ae46f15f57fe7e5
Source dataset
uspto-grants-2016_04
Patent number
US09309265B2

Reaction notes

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