Water → (2,4,5,6-Tetrafluoro[1,1'-biphenyl]-3-yl)methyl trans-3-(2,2-difluoroethenyl)-2,2-dimethylcyclopropanecarboxylate

HRID 1583574Notes

Reaction equation

HRID 1583574 reaction equation
[F:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([F:10])[C:5]([F:11])=[C:4]([F:12])[C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.[F:26][C:27]([F:37])=[CH:28][C@H:29]1[C@H:31]([C:32](Cl)=[O:33])[C:30]1([CH3:36])[CH3:35].O>C(OCC)C>[F:26][C:27]([F:37])=[CH:28][C@H:29]1[C@H:31]([C:32]([O:9][CH2:8][C:7]2[C:2]([F:1])=[C:3]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:4]([F:12])=[C:5]([F:11])[C:6]=2[F:10])=[O:33])[C:30]1([CH3:35])[CH3:36]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 202592392,4,5,6-Tetrafluoro[1,1'-biphenyl]-3-methanolHCID 86740007trans-3-(2,2-Difluoroethenyl)-2,2-dimethylcyclopropanecarbonylchloride

Product 1

HCID 86740509(2,4,5,6-Tetrafluoro[1,1'-biphenyl]-3-yl)methyl trans-3-(2,2-difluoroethenyl)-2,2-dimethylcyclopropanecarboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of 0.97 g (3.8 mmole) of 2,4,5,6-tetrafluoro[1,1'-biphenyl]-3-methanol and 1 ml of dry triethylamine in 8 ml of dry diethyl ether was added 4 ml of a dry diethyl ether solution of trans-3-(2,2-difluoroethenyl)-2,2-dimethylcyclopropanecarbonyl chloride (0.95 mmole/ml). The resultant mixture was stirred at room temperature for approximately 18 hours, then poured into 50 ml of water. The organic phase was separated, washed with a 5% aqueous sodium bicarbonate solution followed by a water wash, then dried over anhydrous magnesium sulfate. The organic phase was filtered, and the filtrate evaporated under reduced pressure to give an oil. The oil was purified by column chromatography on silica gel, eluted with ethyl acetate:hexanes (10:90), to yield 0.92 g of (2,4,5,6-tetrafluoro[1,1'-biphenyl]-3-yl)methyl trans-3-(2,2-difluoroethenyl)-2,2-dimethylcyclopropanecarboxylate as a solid (m.p. 69°-72° C.).

Workup

  1. customThe organic phase was separated
  2. washwashed with a 5% aqueous sodium bicarbonate solution
  3. washwash
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe organic phase was filtered
  6. customthe filtrate evaporated under reduced pressure
  7. customto give an oil
  8. customThe oil was purified by column chromatography on silica gel
  9. washeluted with ethyl acetate:hexanes (10:90)

Sources & evidence

ORD record
ord-4bf454ccfcf848c3a6f9bed47b9f5e7a
Source dataset
uspto-grants-1985_11
Patent number
US04552892

Reaction notes

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