Iodine → HCID 10172919, compound

HRID 2414462Notes

Reaction equation

HRID 2414462 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][CH:3]=1.[Mg].BrCCBr.II.[Br:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[C:22](=[O:23])[O:21][CH2:20]2.[Br-].[Mg+2].[Br-].[CH3:30][N:31]([CH2:33][CH2:34][CH2:35][Mg]Cl)[CH3:32].[Cl-].[NH4+]>O1CCCC1>[Br:16][C:17]1[CH:26]=[CH:25][C:24]([C:22]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)([CH2:35][CH2:34][CH2:33][N:31]([CH3:32])[CH3:30])[OH:23])=[C:19]([CH2:20][OH:21])[CH:18]=1

Participants

10

Reactant 8

HCID 807IodineHCID 78391,2-Dibromoethane2×HCID 99931-Bromo-4-fluorobenzeneHCID 25517Ammonium ChlorideHCID 82241Magnesium BromideHCID 6031445-BromophthalideHCID 5462224Magnesium2×HCID 178483494HCID 178483494, compound

Product 1

HCID 10172919HCID 10172919, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A Grignard solution was prepared from p-fluorobromobenzene (197.6 g) and magnesium turnings (28.15 g) in tetrahydrofuran (1250 ml), in the presence of 1,2-dibromoethane and iodine. The Grignard solution was added to a suspension in tetrahydrofuran (1050 ml) of 5-bromophthalide (150 g) and magnesium bromide, prepared in situ from magnesium and 1,2-dibromoethane over a period of two hours at a temperature below 20° C. After addition was complete, the mixture was stirred, and a Grignard solution of N,N-dimethylaminopropylmagnesium chloride was added to the solution over a period of time at a temperature below 20° C. for more than one hour. The result was mixture was poured into saturated ammonium chloride solution (4500 ml) over a period of time at a temperature below 30° C.

Workup

  1. additionAfter addition

Sources & evidence

ORD record
ord-8c904c4d77a94ce5aabd5dd13f05b120
Source dataset
uspto-grants-2004_11
Patent number
US06812355B2

Reaction notes

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