Water → Methyl 2-chloro-3-(4-[2-(4-hydroxyphenoxy)ethyl]phenyl)propanoate

HRID 1178565Notes

Reaction equation

HRID 1178565 reaction equation
C([O:8][C:9]1[CH:30]=[CH:29][C:12]([O:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([Cl:28])[C:24]([O:26][CH3:27])=[O:25])=[CH:18][CH:17]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.CSC.B(F)(F)F.CCOCC.O>C(Cl)Cl>[Cl:28][CH:23]([CH2:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][CH2:14][O:13][C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:30][CH:29]=2)=[CH:17][CH:18]=1)[C:24]([O:26][CH3:27])=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 1068Dimethyl SulfideHCID 8000Boron trifluoride etherate2×HCID 86600803Methyl 3-(4-(2-[4-(benzyloxy)phenoxy]ethyl)phenyl)-2-chloropropanoate

Product 1

HCID 86600804Methyl 2-chloro-3-(4-[2-(4-hydroxyphenoxy)ethyl]phenyl)propanoateYield 68.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 3-(4-{2-[4-(benzyloxy)phenoxy]ethyl}phenyl)-2-chloropropanoate (1.0 g, 2.4 mmol) and dimethyl sulfide (0.9 g, 14 mmol) was dissolved in 60 ml CH2Cl2. Boron trifluoride etherate (2.0 g, 14 mmol) was added droppwise to the stirred solution. The reaction mixture was stirred for two days at room temperature. Another equivalent (0.4 g, 2.87 mmol) boron trifluoride etherate was added and the stirring was continued overnight. Water was added. The phases were separated and the aqueous phase was extracted twice with CH2Cl2. The organic phases were pooled, washed (water, brine), dried (Na2SO4) and evaporated under reduced pressure. Further purification by preparative HPLC using a gradient of CH3CN/5% CH3CN-waterphase containing 0.1M NH4OAc gave 0.55 g of the desired product (yield 52%) as an oil.

Workup

  1. waitthe stirring was continued overnight
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted twice with CH2Cl2
  4. washwashed (water, brine)
  5. dry with materialdried (Na2SO4)
  6. customevaporated under reduced pressure
  7. customFurther purification by preparative HPLC
  8. additioncontaining 0.1M NH4OAc

Sources & evidence

ORD record
ord-ebea4ad3d5ce41f599907038060213ba
Source dataset
uspto-grants-2007_10
Patent number
US07276539B2

Reaction notes

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