1,4-Dibromobenzene → HCID 70161136, compound

HRID 1636764Notes

Reaction equation

HRID 1636764 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.C([Li])CCC.[CH3:14]/[C:15](=[CH:20]\[CH2:21][CH2:22]/[C:23](/[CH3:33])=[CH:24]/[CH2:25][O:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][O:28]1)/[CH2:16][CH2:17][CH:18]=[O:19]>C1COCC1.CCCCCC>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([CH:18]([OH:19])[CH2:17][CH2:16]/[C:15](/[CH3:14])=[CH:20]/[CH2:21][CH2:22]/[C:23](/[CH3:33])=[CH:24]/[CH2:25][O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 78041,4-DibromobenzeneHCID 14039070HCID 14039070, compoundHCID 178418339Butyllithium

Product 1

HCID 70161136HCID 70161136, compoundYield 45.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of 10.7 g of 1,4-dibromobenzene in 80 ml of absolute THF is cooled to -78° C. and treated within 30 min. with 25.6 ml of 1.6M butyllithium in hexane. After 30 min. 6.08 g of (4E,8E)-(RS)-4,8-dimethyl-10-(tetrahydro-pyran-2-yloxy)-deca-4,8-dienal in 20 ml of THF are added dropwise. After 1 hr. at -78° C. the bath is removed until the suspension has dissolved and subsequently 7.2 ml of acetic acid in 10 ml of ether are added dropwise at -78° C. The solution is poured into saturated ammonium chloride solution/ethyl acetate. The organic phase is washed with saturated sodium bicarbonate solution and 10% sodium chloride solution, dried and evaporated. After silica gel chromatography with hexane/ethyl acetate 95:5 there are obtained 4.3 g of (4E,8E)-1-(4-bromo-phenyl)-4,8-dimethyl-10-(tetrahydro-pyran-2-yloxy)-deca-4,8-dien-1-ol.

Workup

  1. waitAfter 1 hr
  2. customat -78° C. the bath is removed until the suspension
  3. dissolutionhas dissolved
  4. additionsubsequently 7.2 ml of acetic acid in 10 ml of ether are added dropwise at -78° C
  5. additionThe solution is poured into saturated ammonium chloride solution/ethyl acetate
  6. washThe organic phase is washed with saturated sodium bicarbonate solution and 10% sodium chloride solution
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-0396d69f9cdd406a8c808fb2b98c8b92
Source dataset
uspto-grants-2000_03
Patent number
US06034275

Reaction notes

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