4-Bromothioanisole → Bisphenyl-4-thioanisylphosphine

HRID 269427Notes

Reaction equation

HRID 269427 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-f416993864a64314ba1efe9121aa0f3f
Source dataset
uspto-grants-2008_11
Patent number
US07446228B2

Reaction notes

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