Hydrochloric Acid → HCID 22227474, compound

HRID 1744176Notes

Reaction equation

HRID 1744176 reaction equation
[F:1][C:2]1([F:15])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[F:12])[CH:5]=[CH:4][C:3]1([F:14])[F:13].C([Li])(CC)C.[B:21](OC)([O:24]C)[O:22]C.Cl>O1CCCC1.COC(C)(C)C>[F:15][C:2]1([F:1])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([B:21]([OH:24])[OH:22])[C:10]=2[F:12])[CH:5]=[CH:4][C:3]1([F:13])[F:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 22227479HCID 22227479, compoundHCID 178418400CID 53628100

Product 1

HCID 22227474HCID 22227474, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution of 4.8 g of 1,1,2,2,8-pentafluoro-1,2-dihydronaphthalene [(Z3) where R1=H] in 75 ml of tetrahydrofuran was mixed with 11 ml of sec-butyllithium (2M in pentane) at a temperature below −75° C. After 3 g of trimethyl borate had been added, the mixture was stirred at the same temperature for 3 hours and subsequently brought to room temperature overnight. After hydrolysis using 10% hydrochloric acid, 150 ml of tert-butyl methyl ether were added, and the organic phase was separated off, washed with water and sodium chloride solution and dried. The 1,1,2,2,8-pentafluoro-1,2-dihydronaphthalene-7-boronic acid obtained was reacted with the equimolar amount of 4-propylbromobenzene, 2 mol-equivalents of sodium carbonate and 1 mol % of tetrakis(triphenylphosphine)palladium(0) in 50 ml of an ethanol/toluene/water 1:2:1 (vol.) mixture by refluxing for one day. After conventional work-up, the organic fraction was subjected to chromatographic purification (silica gel, toluene/heptane 2:1), the product-containing fractions were combined, the solvent mixture was distilled off under reduced pressure, and the residue was recrystallised from acetonitrile, giving 1.6 g of 1,1,2,2,8-pentafluoro-7-(4-propylphenyl)-1,2-dihydronaphthalene.

Workup

  1. waitsubsequently brought to room temperature overnight
  2. customAfter hydrolysis
  3. additionwere added
  4. customthe organic phase was separated off
  5. washwashed with water and sodium chloride solution
  6. customdried

Sources & evidence

ORD record
ord-c69e2381c4b5482e977390dc6106aebb
Source dataset
uspto-grants-2006_03
Patent number
US07014890B2

Reaction notes

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