Carbon tetrabromide → HCID 18476055, compound

HRID 1251872Notes

Reaction equation

HRID 1251872 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)Br.OC[C:27]1[CH:28]=[CH:29][C:30]([CH2:37][C:38]2[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=2)=[C:31]([CH:36]=1)[C:32]([O:34][CH3:35])=[O:33]>CCOCC>[Br:24][CH2:20][C:27]1[CH:28]=[CH:29][C:30]([CH2:37][C:38]2[CH:39]=[CH:40][C:41]([F:44])=[CH:42][CH:43]=2)=[C:31]([CH:36]=1)[C:32]([O:34][CH3:35])=[O:33]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 18476072HCID 18476072, compound

Product 1

HCID 18476055HCID 18476055, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Triphenylphosphine (9.7 g., 37.0 mmol) and then carbon tetrabromide (12.3 g., 37.0 mmol) were added to a stirred solution of methyl 5-hydroxymethyl-2-(4-fluorobenzyl)benzoate (4.6 g., 16.8 mmol) in anhydrous ether (150 ml) at ambient temperature. After 4 hours the reaction was filtered and the filtrate concentrated under reduced pressure. The product was purified by column chromatography eluting with ethyl acetate/isohexane (5:95) to give methyl 5-bromomethyl-2-(4fluorobenzyl)benzoate as a colourless oil (5.05 g). NMR data (CDCl3) δ: 3.83 (3H, s), 4.37 (2H, s), 4.50 (2H, s), 6.92-6.99 (2H, m), 7.06 7.13 (2H, m), 7.19 (1H, d). 7.43 (1H, dd), 7.95 (1H, d).

Workup

  1. filtrationAfter 4 hours the reaction was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe product was purified by column chromatography
  4. washeluting with ethyl acetate/isohexane (5:95)

Sources & evidence

ORD record
ord-7e9693f6476644a4887e51cb87cd6642
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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