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

HRID 1650367Notes

Reaction equation

HRID 1650367 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-bf635fa7ecbc469db7d164f8e9c7fec1
Source dataset
uspto-grants-1990_05
Patent number
US04924010

Reaction notes

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