Hydrogen Bromide → HCID 53760007, compound

HRID 1732260Notes

Reaction equation

HRID 1732260 reaction equation
[BrH:1].[O:2]([CH2:20][CH:21]([CH3:30])[CH2:22][CH2:23][CH2:24][C:25]([CH3:29])(O)[CH:26]=[CH2:27])[Si:3]([C:16]([CH3:19])([CH3:18])[CH3:17])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(=O)(O)[O-].[Na+]>CCOCC>[O:2]([CH2:20][CH:21]([CH3:30])[CH2:22][CH2:23][CH2:24][C:25]([CH3:29])=[CH:26][CH2:27][Br:1])[Si:3]([C:16]([CH3:19])([CH3:18])[CH3:17])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium Bicarbonate2×HCID 20305779HCID 20305779, compound

Product 1

HCID 53760007HCID 53760007, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 2.25 N hydrogen bromide in ether (1.8 ml) is added to 8-t-butyldiphenylsiloxy-3,7-dimethyl-1-octen-3-ol (1.64 g) in ether (15 ml) dropwise at -70° C. The solution is warmed at 0° C. for 2 hours followed by the addition of solid sodium bicarbonate and then aqueous sodium bicarbonate to pH 7. The layers are separated, the aqueous layer re-extracted with ether and the combined ether extracts are washed with aqueous sodium bicarbonate, brine and dried (Na2SO4). The solids are filtered and the filtrate is evaporated in vacuo to give 8-t-butyldiphenylsiloxy-1-bromo-3,7-dimethyl-oct-2-ene as a yellow oil (1.66 g).

Workup

  1. customThe layers are separated
  2. extractionthe aqueous layer re-extracted with ether
  3. washthe combined ether extracts are washed with aqueous sodium bicarbonate, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationThe solids are filtered
  6. customthe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-660ee9b0e7a748258254fcc98c9db6fe
Source dataset
uspto-grants-1980_12
Patent number
US04237055

Reaction notes

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