HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Bromide ion → 2-(2,4-Difluorophenyl)-1-(4-iodophenyl)ethanone

HRID 850097
Notes
Print preview

Reaction equation

HRID 850097 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH2:4]Br.[Mg].[Br-].CON(C)[C:16]([C:18]1[CH:23]=[CH:22][C:21]([I:24])=[CH:20][CH:19]=1)=[O:17]>CCOCC>[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH2:4][C:16]([C:18]1[CH:23]=[CH:22][C:21]([I:24])=[CH:20][CH:19]=1)=[O:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 259Bromide ionHCID 902971-(Bromomethyl)-2,4-difluorobenzeneHCID 54617564-Iodo-N-methoxy-N-methyl-benzamideHCID 5462224Magnesium

Product 1

HCID 178928972-(2,4-Difluorophenyl)-1-(4-iodophenyl)ethanone

Reagents, catalysts & solvents 1

HCID 3283
Diethyl Ether
Solvent
2×

Procedure

2,4-Difluorobenzyl bromide (23.7 ml, 0.114 mol) was added dropwise to a stirred mixture of magnesium turnings (8.1 g, 0.183 mol) in dry ether (300 ml) under nitrogen. The mixture was warmed initially until initiation of the reaction occurred, and thereafter said bromide was added at such a rate to maintain a gentle reflux. After 1 hour, the resulting solution of the Grignard reagent was added dropwise at -78° C. to a solution of O,N-dimethyl-4-iodobenzenehydroxamic acid (see Preparation 30) (45.71 g, 0.157 mol) in dry ether (300 ml), and the mixture was allowed to warm slowly to room temperature overnight. The mixture was partitioned between saturated aqueous ammonium chloride and ethyl acetate, and the organic solution was separated, dried (MgSO4) and concentrated under reduced pressure, to give the title compound as a white solid, 38.71 g (69%), which was characterised by 1H-N.M.R. spectroscopy.

Workup

  1. temperatureThe mixture was warmed initially until initiation of the reaction
  2. additionwas added at such a rate
  3. temperatureto maintain a gentle reflux
  4. customThe mixture was partitioned between saturated aqueous ammonium chloride and ethyl acetate
  5. customthe organic solution was separated
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d57f373612f64bb6b58edda244fd050d
Source dataset
uspto-grants-2000_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06015825

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes