4-Bromothioanisole → Bisphenyl-4-thioanisylphosphine

HRID 2225048Notes

Reaction equation

HRID 2225048 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[CH:4][CH:3]=1.[CH2:10]([Li])CCC.Cl[P:16]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O1CCCC1>[C:17]1([P:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:10][C:2]2[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[CH:4][CH:3]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 660374-BromothioanisoleHCID 66180ChlorodiphenylphosphineHCID 178418339Butyllithium

Product 1

HCID 69117882Bisphenyl-4-thioanisylphosphine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A cooled solution of 4-bromothioanisole (10.2 g; 0.05 mol) and anhydrous tetrahydrofuran (50 ml) under nitrogen was treated dropwise with 2.5 M n-Butyllithium (19.92 ml; 0.05 mol) in tetrahydrofuran. The cooled mixture was then treated dropwise with a solution of chlorodiphenylphospine (10.0 g; 0.045 mol) and anhydrous tetrahydrofuran (10 ml). The resulting mixture was allowed to warm to room temperature and left to stir for 55 hours. The reaction was quenched with water (500 ml) and extracted with diethyl ether. The combined extracts were dried with magnesium sulphate, filtered and evaporated to dryness to give a yellow solid. Recrystallisation from butanol afforded bisphenyl-4-thioanisylphosphine (XI) as a white solid (3.26 g; 23%).

Workup

  1. waitleft
  2. customThe reaction was quenched with water (500 ml)
  3. extractionextracted with diethyl ether
  4. dry with materialThe combined extracts were dried with magnesium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customto give a yellow solid
  8. customRecrystallisation from butanol

Sources & evidence

ORD record
ord-9e39a81bd39140ab9edd2800e6317e76
Source dataset
uspto-grants-2008_05
Patent number
US07378556B2

Reaction notes

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