Carbon tetrabromide → HCID 25150222, compound

HRID 1170975Notes

Reaction equation

HRID 1170975 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)Br.[CH:25]([C:28]1[CH:29]=[C:30]([CH:42]=[CH:43][C:44]=1[O:45][CH3:46])[O:31][C:32]1[C:39]([Cl:40])=[CH:38][C:35](CO)=[CH:34][C:33]=1[Cl:41])([CH3:27])[CH3:26]>C(OCC)C>[Cl:40][C:39]1[CH:38]=[C:35]([CH:34]=[C:33]([Cl:41])[C:32]=1[O:31][C:30]1[CH:42]=[CH:43][C:44]([O:45][CH3:46])=[C:28]([CH:25]([CH3:26])[CH3:27])[CH:29]=1)[CH2:20][Br:24]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 11131640HCID 11131640, compound

Product 1

HCID 25150222HCID 25150222, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of triphenylphosphine (0.42 g, 1.61 mmol) and CBr4 (0.534 g, 1.61 mmol) in diethyl ether (15.0 mL) at room temperature was added 4-(3′-iso-propyl-4′-methoxyphenoxy)-3,5-dichlorobenzyl alcohol (0.50 g, 1.46 mmol). The reaction mixture was stirred at room temperature for 16 h, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with acetone-hexanes (1:9) to afford 3,5-dichloro-4-(3′-iso-propyl-4′-methoxyphenoxy)benzyl bromide (0.320 g, 54%): 1H NMR (300 MHz, DMSO-d6): δ 7.77 (s, 2 H), 6.82 (m, 2 H), 6.38 (m, 1 H), 4.75 (s, 2 H), 3.75 (s, 3 H), 3.22 (m, 1 H), 1.13 (d, J=6.0 Hz, 6 H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=hexanes-acetone (1:4); Rf=0.46.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product was purified by column chromatography on silica gel
  4. washeluting with acetone-hexanes (1:9)

Sources & evidence

ORD record
ord-082763e2dfdc422595f0c9560be70ab3
Source dataset
uspto-grants-2010_11
Patent number
US07829552B2

Reaction notes

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