1-(Bromomethyl)-2,3-difluoro-benzene → HCID 58951924, compound

HRID 1694788Notes

Reaction equation

HRID 1694788 reaction equation
[CH3:1][N:2]([CH3:18])[S:3]([N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])(=[O:5])=[O:4].C([Li])CCC.[F:24][C:25]1[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:26]=1[CH2:27]Br>O1CCCC1.CCCCCC>[CH3:1][N:2]([CH3:18])[S:3]([N:6]1[CH:10]=[C:9]([CH2:27][C:26]2[CH:29]=[CH:30][CH:31]=[C:32]([F:33])[C:25]=2[F:24])[N:8]=[C:7]1[Si:11]([C:14]([CH3:15])([CH3:17])[CH3:16])([CH3:13])[CH3:12])(=[O:4])=[O:5]

Participants

6

Reactant 3

HCID 5179841-(Bromomethyl)-2,3-difluoro-benzeneHCID 64202092-(tert-Butyldimethylsilyl)-N,N-dimethyl-1H-imidazole-1-sulfonamideHCID 178418339Butyllithium

Product 1

HCID 58951924HCID 58951924, compoundYield 49.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 4.2 g (14.5 mmol) 2-(tert-butyl-dimethyl-silanyl)-imidazole-1-sulfonic acid dimethylamide in 50 ml tetrahydrofuran were added 10.9 ml (17.4 mmol) of a 1.6M butyl lithium solution in hexane at −75° C. After stirring for 20 min 3.6 g (17.4 mmol) 2,3-difluorobenzylbromide was added at −75° C. and the mixture was allowed to reach room temperature overnight. The mixture was partitioned between water and ethyl acetate, re-extracted with ethyl acetate and the combined organic layers are dried over MgSO4, filtered and evaporated. The residue was purified by flash chromatography (silica gel, hexane/ethyl acetate=4:1) to yield 3.0 g (49%) of 2-(tert-butyl-dimethyl-silanyl)-4-(2,3-difluoro-benzyl)-imidazole-1-sulfonic acid dimethylamide as a light yellow solid; MS (ISP): 416.1 ((M+H)+.).

Workup

  1. additionwas added at −75° C.
  2. customThe mixture was partitioned between water and ethyl acetate
  3. extractionre-extracted with ethyl acetate
  4. dry with materialthe combined organic layers are dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash chromatography (silica gel, hexane/ethyl acetate=4:1)

Sources & evidence

ORD record
ord-6caee1f00e234e078be82dfb31df8bf3
Source dataset
uspto-grants-2012_04
Patent number
US08158668B2

Reaction notes

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