Allyl bromide → HCID 58963168, compound

HRID 917527Notes

Reaction equation

HRID 917527 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[C:5]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH:14]([C:18]2[CH:23]=[C:22]([CH2:24][CH3:25])[C:21]([OH:26])=[C:20]([Br:27])[CH:19]=2)[C:15]([O-:17])=[O:16])=[CH:9][CH:8]=1)#[N:6].[C:28]([O-])([O-])=O.[Cs+].[Cs+].[NH4+].[Cl-]>CN(C=O)C>[C:5]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH:14]([C:18]2[CH:23]=[C:22]([CH2:24][CH3:25])[C:21]([O:26][CH2:1][CH:2]=[CH2:3])=[C:20]([Br:27])[CH:19]=2)[C:15]([O:17][CH3:28])=[O:16])=[CH:9][CH:8]=1)#[N:6]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 86595123HCID 86595123, compound

Product 1

HCID 58963168HCID 58963168, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Allyl bromide (0.92 mL, 10.7 mmol) was added drop wise over 5 min to vigorously stirred mixture of 2-(4-cyanophenylamino)-2-(3-bromo-5-ethyl-4-hydroxyphenyl)acetate 3 (3.8 g, 9.76 mmol), Cs2CO3 (3.5 g, 10.74 mmol) and DMF (40 mL). The mixture was stirred vigorously for 4 h, then poured into ½-saturated NH4Cl (400 mL). The mixture was extracted with Et2O (3×100 mL). The combined organic layers were washed with water (3×50 mL), brine (1×100 mL), dried (MgSO4), filtered, and concentrated. The residue was purified by silica gel chromatography (SiO2, gradient elution 10–15–20% ethyl acetate/hexanes) to yield 3.4 g (81%) of methyl 2-(4-cyanophenylamino)-2-(4-(allyloxy)-3-bromo-5-ethylphenyl)acetate 4 as a colorless solid.

Workup

  1. extractionThe mixture was extracted with Et2O (3×100 mL)
  2. washThe combined organic layers were washed with water (3×50 mL), brine (1×100 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (SiO2, gradient elution 10–15–20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-2d7d1b232ad943608d763c90f3dfb567
Source dataset
uspto-grants-2007_09
Patent number
US07273886B2

Reaction notes

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