Water → HCID 22168653, compound

HRID 1392018Notes

Reaction equation

HRID 1392018 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C([O-])([O-])=O.[K+].[K+].[CH2:20](Br)[CH:21]=[CH2:22].O>CN(C=O)C>[NH2:11][C:8]1[CH:9]=[CH:10][C:2]([F:1])=[C:3]([CH:7]=1)[C:4]([O:6][CH2:22][CH:21]=[CH2:20])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 2809972-Fluoro-5-nitrobenzoic acid

Product 1

HCID 22168653HCID 22168653, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Fluoro-5-nitrobenzoic acid (4.16 g, 22.5 mM) was dissolved in DMF (45 ml), and anhydrous K2CO3 (4.65 g, 33.7 mM) added with stirring. Allyl bromide (2.38 ml, 28.1 mM) was run in, the mixture was stirred for 18 hours at ambient temperature before being poured into water (450 ml) and extracted with diethyl ether (3×100 ml). The combined extracts were dried over MgSO4, and evaporated to give a yellow oil (5.4 g). The oil was purified by chromatography on silica, eluting with a mixture of ethyl acetate/hexane (12.5:87.5), to give allyl 2-fluoro-5-nitrobenzoate (4.64 g, 92%). Nmr (CDCl3): δ 4.89 (d, 2H); 5.30-5.50 (m, 2H); 5.90-6.10 (m, 1H); 7.32 (t, 1H); 8.38-8.46 (m, 1H); 8.86 (dd, 1H).

Workup

  1. stirringwas stirred for 18 hours at ambient temperature
  2. extractionextracted with diethyl ether (3×100 ml)
  3. dry with materialThe combined extracts were dried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-370771c28b0e42079fb36a3b4190003c
Source dataset
uspto-grants-2008_03
Patent number
US07342005B2

Reaction notes

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