Carbon tetrabromide → HCID 21195964, compound

HRID 1066821Notes

Reaction equation

HRID 1066821 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:3]=1[CH2:4][O:5][CH2:6][C:7]#[C:8][CH2:9]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:36]>C(OCC)C>[F:1][C:2]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:3]=1[CH2:4][O:5][CH2:6][C:7]#[C:8][CH2:9][Br:36]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 20662455HCID 20662455, compound

Product 1

HCID 21195964HCID 21195964, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 4-(2-fluoro-5-bromobenzyloxy)-but-2-ynyl alcohol (8.9 g, 32.6 mmol) in diethyl ether (109 ml) was treated with triphenylphosphine (11.1 g, 42.4 mmol) and carbon tetrabromide (14.1 g, 42.4 mmol). The cloudy solution was stirred at ambient temperature for about 14 hours. The precipitate was removed by filtration and the filtrate was concentrated. The desired title intermediate was purified from the filtrate by flash chromatography. Yield 9.83 grams (90%) as a clear oil.

Workup

  1. customThe precipitate was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customThe desired title intermediate was purified from the filtrate by flash chromatography

Sources & evidence

ORD record
ord-94c76828543a40f3bccb8c54823aacd7
Source dataset
uspto-grants-2001_06
Patent number
US06245761B1

Reaction notes

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