Carbon tetrabromide → 4-(Bromomethyl)-2-methoxybenzonitrile

HRID 1871194Notes

Reaction equation

HRID 1871194 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7]O)=[CH:5][C:4]=1[O:11][CH3:12])#[N:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:33]>C1COCC1>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][Br:33])=[CH:5][C:4]=1[O:11][CH3:12])#[N:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22016838HCID 22016838, compound

Product 1

HCID 219850074-(Bromomethyl)-2-methoxybenzonitrileYield 85.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of the alcohol from Step E (35.5 g, 218 mmol) in 500 mL of dry THF was cooled to 0° C. Triphenylphosphine was added (85.7 g, 327 mmol), followed by carbontetrabromide (108.5 g, 327 mmol). The reaction was stirred at 0° C. for 30 minutes, then at room temperature for 21 hours. Silica gel was added (ca. 300 g), and the suspension was concentrated in vacuo. The resulting solid was loaded onto a silica gel chromatography column. Purification by flash chromatography (30%-50% EtOAc/hexane) provided the titled product (42 g, 85% yield).

Workup

  1. waitat room temperature for 21 hours
  2. additionSilica gel was added (ca. 300 g)
  3. concentrationthe suspension was concentrated in vacuo
  4. customPurification by flash chromatography (30%-50% EtOAc/hexane)

Sources & evidence

ORD record
ord-51bc463f156b4df39d3cf376826524e5
Source dataset
uspto-grants-2000_08
Patent number
US06103487

Reaction notes

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