2-Bromoanisole → HCID 118057587, compound

HRID 591380Notes

Reaction equation

HRID 591380 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].C([Li])CCC.Cl[P:16]([CH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)[CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1>O1CCCC1>[CH:22]1([P:16]([CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[O:8][CH3:9])[CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

5

Reactant 3

HCID 113582-BromoanisoleHCID 11275743ChlorodicyclopentylphosphineHCID 178418339Butyllithium

Product 1

HCID 118057587HCID 118057587, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere, into a reaction vessel equipped with a dropping funnel were added 0.91 g of 2-bromoanisole and 20 mL of tetrahydrofuran. The resultant solution was cooled down to −78° C., then, 3.4 ml of n-butyllithium (1.62 M/hexane solution) was dropped. The resultant mixture was stirred at the same temperature for 2 hours, then, a solution obtained by dissolving 1.00 g of chlorodicyclopentylphosphine in 13 ml of tetrahydrofuran was dropped at −78° C. The resultant mixture was stirred at room temperature for 3 hours. The resultant reaction mixture was concentrated, and purified by silica gel column chromatography, to obtain 1.19 g of dicyclopentyl(2-methoxyphenyl)phosphine in the form of viscous liquid.

Workup

  1. customUnder a nitrogen atmosphere, into a reaction vessel equipped with a dropping funnel
  2. customa solution obtained
  3. additionwas dropped at −78° C
  4. customThe resultant reaction mixture
  5. concentrationwas concentrated
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-f177f0317dbd40f89e215311cff2a6cf
Source dataset
uspto-grants-2016_01
Patent number
US09238665B2

Reaction notes

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