Carbon tetrabromide → HCID 86624344, compound

HRID 2243807Notes

Reaction equation

HRID 2243807 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([CH:13]=[C:14]([O:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH:15]=1)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:41]>C(Cl)Cl>[Br:41][CH2:2][C:3]1[CH:4]=[C:5]([CH:13]=[C:14]([O:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH:15]=1)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 86624345HCID 86624345, compound

Product 1

HCID 86624344HCID 86624344, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(hydroxymethyl)-5-[(methylsulfonyl)oxy]benzoate (0.284 g, 0.939 mmol) in DCM (5 mL) was added triphenylphosphine (0.370 g, 1.41 mmol) and carbon tetrabromide (0.467 g, 1.41 mmol). After 2 hours, reaction mixture was concentrated in vacuo and purified by flash chromatography (25 g silica, 0-20% EtOAc/hexanes) to give 0.21 g (61%) of tert-butyl 3-(bromomethyl)-5-[(methylsulfonyl)oxy]benzoate. 1H NMR (400 MHz, CDCl3) δ 7.96 (s, 1H), 7.78 (s, 1H), 7.51 (s, 1H), 4.50 (s, 2H), 3.20 (s, 3H), 1.60 (s, 9H).

Workup

  1. customreaction mixture
  2. concentrationwas concentrated in vacuo
  3. custompurified by flash chromatography (25 g silica, 0-20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-e199c4690f32462488f45f8fcaaee326
Source dataset
uspto-grants-2010_03
Patent number
US07678783B2

Reaction notes

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