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

HRID 1935399Notes

Reaction equation

HRID 1935399 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-methoxybenzonitrile

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.

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)
  5. customprovided the

Sources & evidence

ORD record
ord-7f782a0ddaef48079726e1c67f43575e
Source dataset
uspto-grants-2002_05
Patent number
US06387903B1

Reaction notes

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