Water → 2-((2-((6-Bromohexyl)oxy)ethoxy)methyl)-1,3-dichlorobenzene

HRID 503091Notes

Reaction equation

HRID 503091 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:5]=1[CH2:6][O:7][CH2:8][CH2:9][OH:10].[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]Br.O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:10][CH2:9][CH2:8][O:7][CH2:6][C:5]1[C:4]([Cl:3])=[CH:14][CH:13]=[CH:12][C:11]=1[Cl:15]

Participants

7

Reactant 4

HCID 962WaterHCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 13341669Ethanol, 2-((2,6-dichlorophenyl)methoxy)-

Product 1

HCID 668449032-((2-((6-Bromohexyl)oxy)ethoxy)methyl)-1,3-dichlorobenzeneYield 61.2%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent2×

Procedure

50% aq NaOH (1.89 L), 2-(2,6-dichlorobenzyloxy)ethanol (473.2 g), 1,6-dibromohexane (2.44 kg, 5 eq) and tetrabutylammonium bromide (34.1 g, 5 mol %) in toluene (1.89 L) was heated to 55-60° C. for 8-20 h. On cooling water (558 mL) and toluene (558 mL) were added. The aqueous phase was separated and diluted with water (1 L) then back extracted with toluene (1.1 L). The combined toluene extracts were washed twice with water (2.2 L), then evaporated to dryness on a rotary evaporator. The excess 1,6-dibromohexane was removed using a wiped film evaporator, and the resulting crude product chromatographed on silica (5 kg Biotage), eluting with 5% ethyl acetate in petrol 60/80, to give the title compound (503.2 g)−LC RT=7.0 min.

Workup

  1. additionwere added
  2. customThe aqueous phase was separated
  3. additiondiluted with water (1 L)
  4. extractionthen back extracted with toluene (1.1 L)
  5. washThe combined toluene extracts were washed twice with water (2.2 L)
  6. customevaporated to dryness on a rotary evaporator
  7. customThe excess 1,6-dibromohexane was removed
  8. customa wiped film evaporator
  9. customthe resulting crude product chromatographed on silica (5 kg Biotage)
  10. washeluting with 5% ethyl acetate in petrol 60/80

Sources & evidence

ORD record
ord-8876ba81f9c2443ba8afedb8d6b7da4e
Source dataset
uspto-grants-2010_08
Patent number
US07776895B2

Reaction notes

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