Carbon tetrabromide → Methyl 2-(4-fluorophenyl)-4-(3-bromoprop-1-en-1-yl)benzoate

HRID 1019036Notes

Reaction equation

HRID 1019036 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[C:16]([CH:18]=[CH:19][CH2:20]O)[CH:15]=[CH:14][C:9]=2[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:41]C(Br)(Br)Br>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[C:16]([CH:18]=[CH:19][CH2:20][Br:41])[CH:15]=[CH:14][C:9]=2[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 53969551HCID 53969551, compound

Product 1

HCID 54112501Methyl 2-(4-fluorophenyl)-4-(3-bromoprop-1-en-1-yl)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 2-(4-fluorophenyl)-4-(3-hydroxyprop-1-en-1-yl)benzoate (17 g), triphenylphosphine (22.8 g; 87 mmol) and tetrabromomethane (28.8 g; 87 mmol) in dichloromethane (200 ml) was stirred at 0° C. for 1 hour. After filtration of the insoluble material and evaporation to dryness, the residue was purified by flash chromatography eluting with dichloromethanelpetroleum ether (30/70) to give methyl 2-(4-fluorophenyl)-4-(3-bromoprop-1-en-1-yl)benzoate as a mixture of E and Z isomers.

Workup

  1. filtrationAfter filtration of the insoluble material and evaporation to dryness
  2. customthe residue was purified by flash chromatography
  3. washeluting with dichloromethanelpetroleum ether (30/70)

Sources & evidence

ORD record
ord-6934065b6821496c80c99c347f2c737e
Source dataset
uspto-grants-2002_11
Patent number
US06486156B1

Reaction notes

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