Acetic Anhydride → HCID 178467255, compound

HRID 656559Notes

Reaction equation

HRID 656559 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][C:13](=[O:15])[CH:12]=[C:11]([OH:16])[CH2:10]1.[C:17](OC(=O)C)(=[O:19])[CH3:18].CCN(CC)CC>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:10][C:11](=[O:16])[C:12](=[C:17]([OH:19])[CH3:18])[C:13](=[O:15])[CH2:14]1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 579989705-(2-Bromo-4-fluorophenyl)-3-hydroxycyclohex-2-enone

Product 1

HCID 178467255HCID 178467255, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a 500 mL recovery flask was added 5-(2-bromo-4-fluorophenyl)-3-hydroxycyclohex-2-enone (1D) (14.3 g, 50.1 mmol, 1.0 eq.), CH2Cl2 (200 mL), acetic anhydride (6.65 g, 65.2 mmol, 1.3 eq.), Et3N (15.22 g, 150 mmol, 3.0 eq.), and DMAP (catalytic amount). The reaction mixture was stirred overnight at room temperature. Monitoring by LC/MS judged the reaction to be complete. The reaction mixture was concentrated and purified via column chromatography (gradient 70% CH2Cl2/Hex to 100% CH2Cl2) to yield the product as light yellow foam which later became an oil (3.55 g, 22%). The crude material was used in the next step without further purification. ESI-MS: m/z 327.2 (M+H)+.

Workup

  1. customthe reaction
  2. concentrationThe reaction mixture was concentrated
  3. custompurified via column chromatography (gradient 70% CH2Cl2/Hex to 100% CH2Cl2)

Sources & evidence

ORD record
ord-b3d2af5ff81148d9a0feaf0d0c167601
Source dataset
uspto-grants-2011_12
Patent number
US08071766B2

Reaction notes

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