Water → HCID 66672072, compound

HRID 1158178Notes

Reaction equation

HRID 1158178 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[CH:17]=[C:18]([C:26]3[CH:31]=[CH:30][C:29]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:28][CH:27]=3)[CH:19]=[CH:20][C:21]=2[CH2:22][CH2:23]CO)[CH:8]=[CH:9][C:10]=1[N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])([CH3:4])([CH3:3])[CH3:2].C(P(CCCCCCCC)CCCCCCCC)CCCCCCC.[C:62]([Br:66])(Br)(Br)Br.O>C(OCC)C>[Br:66][CH2:62][CH2:23][CH2:22][C:21]1[CH:20]=[CH:19][C:18]([C:26]2[CH:27]=[CH:28][C:29]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:30][CH:31]=2)=[CH:17][C:16]=1[C:7]1[CH:8]=[CH:9][C:10]([N:11]([CH2:12][CH3:13])[CH2:14][CH3:15])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11205Carbon tetrabromideHCID 20851TrioctylphosphineHCID 11533228HCID 11533228, compound

Product 1

HCID 66672072HCID 66672072, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

6.4 g of ethyl 3″-tert-butyl-4″-diethylamino-4′-(3-hydroxypropyl)-[1,1′;3′,1″]terphenyl-4-carboxylate obtained in Example 32c (13 mmol) are dissolved in 128 mL of diethyl ether. The dissolution is performed under cold conditions (0° C.), and 11.4 mL of trioctylphosphine are then added (26 mmol) followed by addition of a solution of 8.5 g of carbon tetrabromide (26 mmol) dissolved in 10 volumes of Et2O added dropwise. The reaction medium is stirred at 0° C. for 30 minutes and then for 1 hour 30 minutes at room temperature. The reaction is stopped by adding 100 mL of water and then extracted with 100 mL of ethyl acetate. The organic phases are washed with 400 mL of water and then dried over magnesium sulfate. The solvents are evaporated off and the residue is then purified by chromatography on silica gel (eluent: 9/1 heptane/ethyl acetate). 6 g of ethyl 4′-(3-bromopropyl)-3″-tert-butyl-4″-diethylamino[1,1′;3′,1″]terphenyl-4-carboxylate are obtained (yield=83%) in the form of a thick brown oil.

Workup

  1. dissolutionThe dissolution
  2. additionare then added (26 mmol)
  3. additionadded dropwise
  4. waitfor 1 hour 30 minutes at room temperature
  5. extractionextracted with 100 mL of ethyl acetate
  6. washThe organic phases are washed with 400 mL of water
  7. dry with materialdried over magnesium sulfate
  8. customThe solvents are evaporated off
  9. customthe residue is then purified by chromatography on silica gel (eluent: 9/1 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-3cb7c100a05a4d89b7bee963a8c2b35b
Source dataset
uspto-grants-2010_10
Patent number
US07807708B2

Reaction notes

Loading…