Carbon tetrabromide → HCID 89544562, compound

HRID 2283434Notes

Reaction equation

HRID 2283434 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])=[C:6]([F:16])[C:5]([CH:17](O)[CH2:18][CH3:19])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:41]>C(Cl)Cl>[Br:41][CH:17]([C:5]1[C:6]([F:16])=[C:7]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])[C:2]([Cl:1])=[CH:3][CH:4]=1)[CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 89544874HCID 89544874, compound

Product 1

HCID 89544562HCID 89544562, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step 2 [6-Chloro-2-fluoro-3-(1-hydroxy-propyl)-phenyl]-phenyl-methanone (760 mg; 2.6 mmol) was dissolved in DCM (20 ml), treated with triphenylphosphine (1.095 g; 1.6 equiv.) and carbon tetrabromide (1.275 g; 1.5 equiv.) and stirred at room temperature overnight. The reaction mixture was evaporated then purified by flash column chromatography eluting with 0 to 20% EtOAc/petroleum ether. Product containing fractions were combined and evaporated to give 650 mg of [3-(1-Bromo-propyl)-6-chloro-2-fluoro-phenyl]-phenyl-methanone as a colourless gum. 1H NMR (400 MHz, DMSO-d6): 7.89-7.69 (4H, m), 7.69-7.54 (3H, m), 5.34 (1H, dd), 2.38-2.12 (2H, m), 0.99 (3H, t).

Workup

  1. customThe reaction mixture was evaporated
  2. customthen purified by flash column chromatography
  3. washeluting with 0 to 20% EtOAc/petroleum ether
  4. additionProduct containing fractions
  5. customevaporated

Sources & evidence

ORD record
ord-3945eb92219640348408022444c8ee36
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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