Chlorosuccinimide → HCID 15170304, compound

HRID 1723050Notes

Reaction equation

HRID 1723050 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:8][CH2:7][CH2:6][C:5]2[CH:9]=[CH:10][CH:11]=[C:12]([C:13]([OH:15])=[O:14])[C:4]=2[O:3]1.[Cl:17]N1C(=O)CCC1=O>CN(C=O)C.C(OCC)(=O)C>[CH3:1][C:2]1([CH3:16])[CH2:8][CH2:7][CH2:6][C:5]2[CH:9]=[C:10]([Cl:17])[CH:11]=[C:12]([C:13]([OH:15])=[O:14])[C:4]=2[O:3]1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 15170301HCID 15170301, compound

Product 1

HCID 15170304HCID 15170304, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3.6 g (16.4 mmol) of 2,2-dimethyl-2,3,4,5-tetrahydro-1-benzoxepin-9-carboxylic acid in 20 ml of DMF is added 2.6 g (19.7 mmol) of N-chlorosuccinimide in one portion at room temperature. The resulting solution is stirred for 31/2 days. The reaction mixture is then diluted with ethyl acetate washed with water, and the organic layer is dried (MgSO4), filtered and concentrated to obtain 2,2-dimethyl-7-chloro-2,3,4,5-tetrahydro-1-benzoxepin-9-carboxylic acid.

Workup

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

Sources & evidence

ORD record
ord-115a94f088354f698c6b8d02e7a8d410
Source dataset
uspto-grants-1989_08
Patent number
US04859683

Reaction notes

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