Water → Halfenprox

HRID 2231341Notes

Reaction equation

HRID 2231341 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:26])([CH3:25])[CH2:9][O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:13]=2)=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[Br:33][C:34](Br)([F:36])[F:35].O>CN1C(=O)N(C)CC1>[CH3:25][C:8]([C:5]1[CH:4]=[CH:3][C:2]([O:1][C:34]([Br:33])([F:36])[F:35])=[CH:7][CH:6]=1)([CH2:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:13]=1)[CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 6382DibromodifluoromethaneHCID 157700Phenol, 4-(1,1-dimethyl-2-((3-phenoxyphenyl)methoxy)ethyl)-HCID 23665647Potassium tert-butoxide

Product 1

HCID 10140464HalfenproxYield 99.4%

Reagents, catalysts & solvents 1

HCID 66611,3-Dimethyl-2-imidazolidinoneSolvent2×

Procedure

A solution of 21.6 g of 3-phenoxybenzyl 2-(4-hydroxyphenyl)-2-methylpropyl ether and 13.9 g of potassium t-butoxide in 120 ml of DMI was added dropwise to a mixture of 80 g of dibromodifluoromethane and 50 ml of DMI with stirring for 30 minutes at 50° to 60° C., and the mixture was maintained at this temperature for 3 hours. The reaction mixture was poured into water and extracted with toluene. The toluene solution was washed with dilute hydrochloric acid and water in this order, and dried. Toluene was evaporated under reduced pressure to give 29.4 g of an oily residue. The oily residue was purified by column chromatography [silica gel: 600 g; eluent: toluene/hexane (1:1)] to give 12.4 g of the desired 3-phenoxybenzyl 2-(4-difluorobromomethoxyphenyl)-2-methylpropyl ether.

Workup

  1. temperaturethe mixture was maintained at this temperature for 3 hours
  2. extractionextracted with toluene
  3. washThe toluene solution was washed with dilute hydrochloric acid and water in this order
  4. customdried
  5. customToluene was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9686631ec3cf47af941182a6adc113d3
Source dataset
uspto-grants-1988_11
Patent number
US04782094

Reaction notes

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