Triphenylphosphine → HCID 21182289, compound

HRID 2374122Notes

Reaction equation

HRID 2374122 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[Br:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]2[CH:44]=[CH:43][C:42]([OH:45])=[CH:41][CH:40]=2)=[CH:35][CH:34]=1.[Br:46][C:47]1[CH:52]=[CH:51][C:50](C2C=CC(OCCCCCCO)=CC=2)=[CH:49][CH:48]=1>C1COCC1>[Br:32][C:33]1[CH:34]=[CH:35][C:36]([C:39]2[CH:44]=[CH:43][C:42]([O:45][CH2:52][CH2:51][CH2:50][CH2:49][CH2:48][CH2:47][Br:46])=[CH:41][CH:40]=2)=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 950934-Bromo-4'-hydroxybiphenylHCID 5462977Diethyl azodicarboxylateHCID 69205003HCID 69205003, compound

Product 1

HCID 21182289HCID 21182289, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of triphenylphosphine (3.46 g, 0.013 mol) and DEAD (2.30 g, 0.012 mol) in dry cold THF (100 ml) was added dropwise over 10 min to a solution of 4-bromo-4′-hydroxybiphenyl (3.00 g, 0.012 mol) and 4-bromo-4′-(6-hydroxyhexyloxy)biphenyl (2.20 g, 0.012 mol) (prepared as described in Example 4 step 2 above) in dry THF (50 ml) stirring at room temperature. The reaction mixture was left stirring overnight The reaction product was extracted into diethyl ether (2×200 ml), and the combined ethereal solutions were washed with water and dried (MgSO4). The crude product was adsorbed onto silica gel and purified by column chromatography [DCM-petroleum fraction (bp 40-60° C.), 1:6] and recrystallised from ethanol to give white crystals.

Workup

  1. waitThe reaction mixture was left
  2. stirringstirring overnight The reaction product
  3. extractionwas extracted into diethyl ether (2×200 ml)
  4. washthe combined ethereal solutions were washed with water
  5. dry with materialdried (MgSO4)
  6. custompurified by column chromatography [DCM-petroleum fraction (bp 40-60° C.), 1:6]
  7. customrecrystallised from ethanol
  8. customto give white crystals

Sources & evidence

ORD record
ord-6adc3c0f105840d59c2c799397956b4a
Source dataset
uspto-grants-2008_12
Patent number
US07462427B2

Reaction notes

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