1,1-Dibromoethane → Cuminaldehyde

HRID 445156Notes

Reaction equation

HRID 445156 reaction equation
NC1C(O)=CC=CC=1[C:9]([C:11]1[CH:16]=[CH:15][C:14]([CH:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=1)=[O:10].BrC(Br)C.C(N(C(C)C)C(C)C)C>O1CCOCC1>[CH:17]([C:14]1[CH:15]=[CH:16][C:11]([CH:9]=[O:10])=[CH:12][CH:13]=1)([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 112011,1-DibromoethaneHCID 81531DiisopropylethylamineHCID 60112845(2-Amino-3-hydroxy-phenyl)-(4-isopropyl-phenyl)-methanone

Product 1

HCID 326Cuminaldehyde

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 0.5 g (1.96 mmol) (2-amino-3-hydroxy-phenyl)-(4-isopropyl-phenyl)-methanone, 0.85 ml (9.8 mmol) dibromoethane and 0.67 ml (3.9 mmol) N-ethyl-diisopropylamine in 3 ml dioxane is heated to 100° for 5 d. After extraction with water/dichloromethane the crude product is purified by flash chromatography using a gradient going from hexanes to hexanes/ethyl acetate 7:1 to yield (3,4-dihydro-2.H.-benzo[1,4]oxazin-5-yl)-(4-isopropyl-phenyl)-methanone.

Workup

  1. extractionAfter extraction with water/dichloromethane the crude product
  2. customis purified by flash chromatography

Sources & evidence

ORD record
ord-a405948dbcb4443e819cbfeb0a2b249a
Source dataset
uspto-grants-2013_07
Patent number
US08476286B2

Reaction notes

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