Iodine → 6-Bromohexyl 4-(3-iodophenyl)butyl ether

HRID 2118319Notes

Reaction equation

HRID 2118319 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[C:9]([CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[C:23]([Br:24])=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:10]=[CH:11][CH:12]=1.[I:25]I.S(=O)(O)[O-].[Na+]>CCCCCC.C1COCC1.O>[I:25][C:7]1[CH:8]=[C:9]([CH2:13][CH2:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][Br:24])[CH:10]=[CH:11][CH:12]=1

Participants

8

Reactant 4

HCID 807IodineHCID 23665763Sodium BisulfiteHCID 691193926-Bromophenyl 4-(3-bromophenyl)butyl etherHCID 178418339Butyllithium

Product 1

HCID 691198836-Bromohexyl 4-(3-iodophenyl)butyl etherYield 70.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of n-butyl lithium in hexane (1.6 M; 50 ml) was added to a stirred solution of 6-bromophenyl 4-(3-bromophenyl)butyl ether (21 g) in dry THF (150 ml) at −85° C. under nitrogen. After 15 min a solution of iodine (19.8 g) in THF (100 ml) was added dropwise over 20 min. The solution was then allowed to warm up to 0° C. and aqueous sodium bisulphite was added. The mixture was poured into water and extracted into ether. The combined extracts were dried (Na2SO4) and evaporated. The residue was purified by flash silica gel column chromatography (1 kg) eluting with cyclohexane-ether (9:1). The appropriate fractions were evaporated to give the title compound (17 g). LCMS RT=4.41 min.

Workup

  1. extractionextracted into ether
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. customevaporated
  4. customThe residue was purified by flash silica gel column chromatography (1 kg)
  5. washeluting with cyclohexane-ether (9:1)
  6. customThe appropriate fractions were evaporated

Sources & evidence

ORD record
ord-b40e31a4ab1240dcad98430e33960285
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

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