Carbon tetrabromide → 5-(bromomethyl)-2,2-difluorobenzo[d][1,3]dioxole

HRID 594317Notes

Reaction equation

HRID 594317 reaction equation
[F:1][C:2]1([F:13])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH2:11]O)=[CH:10][C:4]=2[O:3]1.C(Br)(Br)(Br)[Br:15].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[Br:15][CH2:11][C:9]1[CH:8]=[CH:7][C:5]2[O:6][C:2]([F:13])([F:1])[O:3][C:4]=2[CH:10]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 12814281(2,2-Difluoro-1,3-dioxaindan-5-yl)methanol

Product 1

HCID 203113835-(bromomethyl)-2,2-difluorobenzo[d][1,3]dioxole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2,2-difluorobenzo[d][1,3]dioxol-5-yl)methanol (120 mg; 0.63 mmol) in anh. DCM (5 ml) was treated at rt with CBr4 (211 mg; 0.63 mmol), and with PPh3 (167 mg; 0.63 mmol). The resulting mixture was further stirred at rt, under nitrogen, for 17 h. Concentration to dryness under reduced pressure, and subsequent purification by FC (DCM) afforded 5-(bromomethyl)-2,2-difluorobenzo[d][1,3]dioxole as a pale yellow oil which was directly used for the next reaction.

Workup

  1. concentrationConcentration to dryness
  2. customunder reduced pressure, and subsequent purification by FC (DCM)

Sources & evidence

ORD record
ord-66d88aac48804845b2cf3625f794799d
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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