Triphenylphosphine → HCID 11465985, compound

HRID 2113475Notes

Reaction equation

HRID 2113475 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]([Br:14])[O:9][C:10]2=[O:13])=[CH:6][CH:5]=1)([O-])=O.[C:15]1([P:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(OCC)(=O)CC>[Br-:14].[NH2:1][C:4]1[CH:12]=[C:11]2[C:7](=[CH:6][CH:5]=1)[CH:8]([P+:21]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[O:9][C:10]2=[O:13]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 11459567HCID 11459567, compound

Product 1

HCID 11465985HCID 11465985, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 7749Ethyl PropionateSolvent2×

Procedure

A solution of 6-nitro-3-bromo-3H-isobenzofuran-1-one (8.7 g, 0.034 mol) in ethyl propionate (464 ml) was heated to 70-75° C., and stirred while 313 ml of an ethyl propionate solution of triphenyl phosphine (36 g, 0.137 mol, 4 eq) were added dropwise over a time of 7 hours. Heating and stirring were continued overnight, and then the mixture was cooled down to room temperature. The precipitate was collected, dried up under vacuum and purified by flash chromatography over silica gel. A gradient of dichloromethane-methanol-acetic acid, from 97-3-0 to 93-5-2 was used as the eluant, to yield 6.2 g of the title compound. [M]+=410; HPLC r.t. 4.72; 1H-NMR (DMSO-d6), diagnostic signals (ppm): 6.01 (br. s, 2H exchangeable with deuterated water), 6.49 (dd, 1H), 6.80 (d, 1H), 6.87 (d, 1H), 7.62-8.00 (m, 15H), 8.17 (s, 1H).

Workup

  1. additionwere added dropwise over a time of 7 hours
  2. temperatureHeating
  3. customThe precipitate was collected
  4. customdried up under vacuum
  5. custompurified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-d61159aa79aa4fbd80083ab4c7b1f89b
Source dataset
uspto-grants-2008_10
Patent number
US07432263B2

Reaction notes

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