Diethyl Ether → HCID 15085698, compound

HRID 2166318Notes

Reaction equation

HRID 2166318 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:15])[C:10]([CH3:14])([CH3:13])[CH:11]=O.[C:16]([Br:20])(Br)(Br)[Br:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOCC.[Cl:45]CCl>>[Br:17][C:16]([Br:20])=[CH:11][C:10]([CH3:14])([CH3:13])[C:9]([NH:8][C:3]1[CH:4]=[CH:5][C:6]([Cl:45])=[CH:7][CH:2]=1)=[O:15]

Participants

6

Reactant 5

HCID 3283Diethyl EtherHCID 6344Dichloromethane2×HCID 11205Carbon tetrabromideHCID 11776Triphenylphosphine2×HCID 23039283HCID 23039283, compound

Product 1

HCID 15085698HCID 15085698, compound

Procedure

Using the procedure described by Corey and Fuchs, Tetrahedron Letters, p 3769, 1972, N-(chlorophenyl)-2,2-dimethyl-3-oxopropanamide (1 g), which was prepared as described in Example 9, and carbon tetrabromide (3 g) were dissolved in 75 mL of dichloromethane, the solution was cooled, and triphenylphosphine (4.6 g) in 20 mL of dichloromethane was added dropwise over 30 minutes. After the solution was stirred one hour, an additional 1 g of triphenylphosphine was added. Ether (100 mL) was then added, and the solution was filtered through a silica gel column to remove triphenylphosphine oxide (eluting with ether). The filtrate fractions which contained the product were concentrated to give the title compound, a solid, m.p. 104° C.

Workup

  1. customwas prepared
  2. temperaturethe solution was cooled
  3. filtrationthe solution was filtered through a silica gel column
  4. customto remove triphenylphosphine oxide (eluting with ether)
  5. concentrationwere concentrated

Sources & evidence

ORD record
ord-e6ef97180c2a474db28727631f9d2db3
Source dataset
uspto-grants-1990_07
Patent number
US04944795

Reaction notes

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