Chlorosuccinimide → 7-Chloro-2,3,4,5-tetrahydro-1-benzoxepin-9-carboxylic acid

HRID 1722642Notes

Reaction equation

HRID 1722642 reaction equation
[O:1]1[C:7]2[C:8]([C:12]([OH:14])=[O:13])=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:15]N1C(=O)CCC1=O>CN(C=O)C.C(OCC)(=O)C>[Cl:15][C:10]1[CH:9]=[C:8]([C:12]([OH:14])=[O:13])[C:7]2[O:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]=2[CH:11]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 127011502,3,4,5-Tetrahydro-1-benzoxepin-9-carboxylic acid

Product 1

HCID 145020977-Chloro-2,3,4,5-tetrahydro-1-benzoxepin-9-carboxylic acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.7 g (8.9 mmol) of 2,3,4,5-tetrahydro-1-benzoxepin-9-carboxylic acid in 5 ml of DMF is added 1.41 g (10.6 mmol) of N-chlorosuccinimide (NCS) in one portion at room temperature. The solution is stirred overnight and then diluted with ethyl acetate and washed with water. The organic layer is then dried (MgSO4), filtered and concentrated to obtain 7-chloro-2,3,4,5-tetrahydro-1-benzoxepin-9-carboxylic acid.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer is then dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-63d070b3c59c4877ac481d5a274b9914
Source dataset
uspto-grants-1989_08
Patent number
US04857517

Reaction notes

Loading…