Bromine → HCID 86753061, compound

HRID 2392940Notes

Reaction equation

HRID 2392940 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6](/[C:14](/[CH3:18])=[CH:15]/[CH:16]=[O:17])[CH:5]=[CH:4][C:3]1=2.[Br:20]Br.C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[Br:20]/[C:15](=[C:14](/[C:6]1[CH:5]=[CH:4][C:3]2[C:2]([CH3:19])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]=2[CH:7]=1)\[CH3:18])/[CH:16]=[O:17]

Participants

5

Reactant 3

HCID 24408BromineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86753060HCID 86753060, compound

Product 1

HCID 86753061HCID 86753061, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-75 °C

Procedure

2.86 g of (E)-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-but-2-enal were dissolved in 16 ml of CH2Cl2 and cooled to -75° C. 1.1 eq. of Br2 (0.63 ml), dissolved in 3 ml of CH2Cl2, was added drop by drop and the mixture kept for 10 minutes at this temperature. TLC indicated the formation of the dibromide. 4.98 ml of DBU was then added all at once and the temperature raised to 0° C. After 1/2 hour the reaction mixture was poured onto crushed ice/HCl, extracted with EtOEt, washed twice with brine, dried over Na2 SO4 and the solvents removed i.V. Flash chromatography (silica gel, hexane/AcOEt=96:4) yielded 0.95 g of the labile (E)-2-bromo-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-but-2-enal as yellow crystals of m.p. 115°-117° C. Double bond geometry was proven by NOE.

Workup

  1. additionwas added drop by drop
  2. temperatureraised to 0° C
  3. additionAfter 1/2 hour the reaction mixture was poured
  4. extractionextracted with EtOEt
  5. washwashed twice with brine
  6. customdried over Na2 SO4
  7. customthe solvents removed i.V

Sources & evidence

ORD record
ord-04a5572b0c7c41cbbd7dbb6b5429f010
Source dataset
uspto-grants-1998_09
Patent number
US05801253

Reaction notes

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