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Carbon tetrabromide → 3-[2-Bromomethyl-4-(tert-butyldiphenylsilanyloxy)phenyl]propionic acid tert-butyl ester

HRID 1181124
Notes
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Reaction equation

HRID 1181124 reaction equation
[C:1]([O:5][C:6](=[O:35])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][Si:16]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][C:10]=1[CH2:33]O)([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:56]>C1COCC1>[C:1]([O:5][C:6](=[O:35])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][Si:16]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][C:10]=1[CH2:33][Br:56])([CH3:4])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 589792063-[4-(tert-Butyldiphenylsilanyloxy)-2-hydroxymethylphenyl]propionic acid tert-butyl ester

Product 1

HCID 589793453-[2-Bromomethyl-4-(tert-butyldiphenylsilanyloxy)phenyl]propionic acid tert-butyl esterYield 86.2%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

A 200 mL round bottomed flask was charged with 3-[4-(tert-butyldiphenylsilanyloxy)-2-hydroxymethylphenyl]propionic acid tert-butyl ester (3.03 g, 6.18 mmol), anhydrous THF (75 mL), and then triphenylphosphine (3.24 g, 12.4 mmol) and CBr4 (4.10 g, 12.4 mmol). The yellow mixture was stirred at ambient temperature under a nitrogen atmosphere for 1 h and was concentrated. The residue was diluted with EtOAc (500 mL). The organic layer was washed with brine (2×), dried (Na2SO4), and concentrated to a solid. The crude product was purified using a Biotage medium pressure chromatography system (EtOAc:hexanes 10:90) to give a yellow oil (2.95 g, 86%), MS (ES) m/e 572 (M+NH4).

Workup

  1. concentrationwas concentrated
  2. additionThe residue was diluted with EtOAc (500 mL)
  3. washThe organic layer was washed with brine (2×)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to a solid
  6. customThe crude product was purified

Sources & evidence

ORD record
ord-30d82aef0da1469092a2e1dfed64bf8c
Source dataset
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07282501B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes