Carbon tetrabromide → HCID 23045316, compound

HRID 2108122Notes

Reaction equation

HRID 2108122 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]1([CH2:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][CH2:35]O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(Br)(Br)(Br)[Br:38]>ClCCl>[Br:38][CH2:35][CH2:34][CH2:33][O:32][CH2:31][CH2:30][O:29][CH2:28][CH2:27][CH2:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 23045279HCID 23045279, compound

Product 1

HCID 23045316HCID 23045316, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triphenylphosphine (12.59 g), in dry dichloromethane was added dropwise over 20 min to a stirred solution of 3-[2-(3-phenylpropoxy)ethoxy]-1-propanol (8.8 g) and carbon tetrabromide (15.92 g) in dry dichloromethane (170 ml) at 0° C. under nitrogen. The solution was allowed to warm to room temperature and stirred under nitrogen for 30 min. The solution was concentrated to ca 30 ml and then purified by FCC eluting with System B (0:10→2:3) to give the title compound (9.94 g) as an oil. T.l.c. (System B 1:1) Rf 0.50

Workup

  1. concentrationThe solution was concentrated to ca 30 ml
  2. custompurified by FCC
  3. washeluting with System B (0:10→2:3)

Sources & evidence

ORD record
ord-34f5556d9a8748ea9bb551e2d1e61e25
Source dataset
uspto-grants-1990_06
Patent number
US04937268

Reaction notes

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