Triethylamine → HCID 86670559, compound

HRID 1403384Notes

Reaction equation

HRID 1403384 reaction equation
[C:1]([Br:5])(Br)(Br)[Br:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCN(CC)CC.[F:32][C:33]1[CH:40]=[CH:39][C:36]([CH:37]=O)=[C:35]([OH:41])[CH:34]=1>ClCCl>[Br:2][C:1]([Br:5])=[CH:37][C:36]1[CH:39]=[CH:40][C:33]([F:32])=[CH:34][C:35]=1[OH:41]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 27792684-Fluoro-2-hydroxybenzaldehyde

Product 1

HCID 86670559HCID 86670559, compoundYield 27.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of CBr4 (5.6 g, 17.1 mmoL) in dichloromethane (100 mL) was added PPh3 (7 g, 26.69 mmol) at 0° C., 30 min later, NEt3 (4.3 g, 42.6 mmol) and 4-fluoro-2-hydroxybenzaldehyde (1 g, 7.14 mmol) was added slowly. After stirring for 30 mins at room temperature, the resulting mixture was concentrated under reduced pressure to afford a residue, which was purified by a silica gel column with 5% ethyl acetate in petroleum ether to afford 2-(2,2-dibromoethenyl)-5-fluorophenol as a white solid (0.58 g, 27%).

Workup

  1. concentrationthe resulting mixture was concentrated under reduced pressure
  2. customto afford a residue, which
  3. customwas purified by a silica gel column with 5% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-4fc89b27007f47e2a535f17f2f475f97
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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